[ CAS No. 93-09-4 ] {[proInfo.proName]}

Name: 93-09-4|2-Naphthoic acid|98%
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Quality Control of [ 93-09-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 93-09-4 ]

Product Details of [ 93-09-4 ]

CAS No. :	93-09-4	MDL No. :	MFCD00004101
Formula :	C₁₁H₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	172.18	Pubchem ID :	-
Synonyms :	Naphthalene-2-carboxylic acid

Calculated chemistry of [ 93-09-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	50.91
TPSA :	37.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.64
Log Po/w (XLOGP3) :	3.28
Log Po/w (WLOGP) :	2.54
Log Po/w (MLOGP) :	2.64
Log Po/w (SILICOS-IT) :	2.35
Consensus Log Po/w :	2.49

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.48
Solubility :	0.0574 mg/ml ; 0.000333 mol/l
Class :	Soluble
Log S (Ali) :	-3.74
Solubility :	0.0315 mg/ml ; 0.000183 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.44
Solubility :	0.0622 mg/ml ; 0.000361 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 93-09-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 93-09-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 93-09-4 ]
Downstream synthetic route of [ 93-09-4 ]

[ 93-09-4 ] Synthesis Path-Upstream 1~9

1
[ 93-09-4 ]
[ 67878-76-6 ]

Yield	Reaction Conditions	Operation in experiment
38%	With sodium hydroxide; sulfuric acid; bromine; iodine In methanol; acetic acid	Step (1) Preparation of Methyl 5-Bromo-2-naphthoate To a boiling solution of 2-naphthoic acid (200 g, 1.16 mol) in acetic acid (1000 mL) was added dropwise bromine (60 mL, 2.2 mol) containing 5.0 g of iodine. After the addition was complete, the solution was refluxed for an additional 0.5 hour. After cooling the precipitated product was isolated by filtration, washed with acetic acid and water. The crude acid was treated with hot 1N sodium hydroxide solution (1000 mL). The resulting suspension was filtered to give the sodium salt of the carboxylic acid (107 g). On cooling the filtrate furnished an additional material (43 g, total 150 g). This was suspended in methanol (1L) and concentrated sulfuric acid (68 mL) was added gradually. This suspension was refluxed for 18 hours. After cooling, the resulting solution was evaporated to dryness in vacuo and the residue partitioned between methylene chloride and water. The aqueous layer was extracted with methylene chloride and the combined organic layers were washed with saturated sodium bicarbonate solution and with water. This was dried (MgSO₄) and evaporated in vacuo to give the crude title compound (116.5 g, 38percent) as an oil which crystallized slowly on standing to an off-white solid, m.p. 65°-68° C.
38%	With sodium hydroxide; sulfuric acid; bromine; iodine In methanol; acetic acid	Step (1) Preparation of Methyl 5-Bromo-2-naphthoate To a boiling solution of 2-naphthoic acid (200 g, 1.16 mol) in acetic acid (1000 mL) was added dropwise bromine (60 mL, 2.2 mol) containing 5.0 g of iodine. After the addition was complete, the solution was refluxed for an additional 0.5 hour. After cooling the precipitated product was isolated by filtration, washed with acetic acid and water. The crude acid was treated with hot 1N sodium hydroxide solution (1000 mL). The resulting suspension was filtered to give the sodium salt of the carboxylic acid (107 g). On cooling the filtrate furnished an additional material (43 g, total 150 g). This was suspended in methanol (1 L) and concentrated sulfuric acid (68 mL) was added gradually. This suspension was refluxed for 18 hours. After cooling, the resulting solution was evaporated to dryness in vacuo and the residue partitioned between methylene chloride and water. The aqueous layer was extracted with methylene chloride and the combined organic layers were washed with saturated sodium bicarbonate solution and with water. This was dried (MgSO₄) and evaporated in vacuo to give the crude title compound (116.5 g, 38percent) as an oil which crystallized slowly on standing to an off-white solid, m.p. 65°-68° C.

Reference： [1] Patent: US4897405, 1990, A,
[2] Patent: US4966975, 1990, A,

2
[ 67-56-1 ]
[ 93-09-4 ]
[ 67878-76-6 ]

Reference： [1] Journal of Fluorine Chemistry, 1988, vol. 38, p. 139 - 152

3
[ 93-09-4 ]
[ 835-58-5 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1974, vol. 10, p. 1715 - 1720[2] Zhurnal Organicheskoi Khimii, 1974, vol. 10, p. 1698 - 1704

4
[ 93-09-4 ]
[ 1013-83-8 ]

Yield	Reaction Conditions	Operation in experiment
53.4%	With bromine; iodine In acetic acid for 0.5 h; Heating / reflux	To a boiling solution of 2-naphthoic acid (10.00 g, 58.14 mmol) in acetic acid (50 mL) is added dropwise bromine (3 mL) containing iodine (0.25 g). After the addition is complete, the solution is refluxed for 0.5 hr. A white precipitate forms during cooling and is isolated by filtration, washed with acetic acid and then water. The solid is triturated in methanol (100 mL) and 7.01 g (53.4percent yield) of the desired product is obtained as a white solid. m.p. 248-250° C. ¹H NMR (300 MHz, CD₃OD): δ 8.94 (d, J=1.8 Hz, 1H), 8.52-8.42 (m, 3H), 8.27 (dd, J=1.8, 7.5 Hz, 1H), 7.79 (t, J=8.4 Hz, 1H).
46%	With bromine In acetic acid for 0.583333 h; Heating / reflux	Preparation 3 [0106] Preparation of 6-Iodo-1-methoxy-naphthalene. [CHEMMOL-00022] [0107] Preparation of 5-Bromo-2-naphthalenecarboxylic acid. [0108] 2-Naphthoic acid (50;0 g, 0.290 mol), glacial acetic acid (250 mL), bromine (15 mL, 0.291 mol) and iodine (1.3 g, 0.005 mol) were combined in a flask under N2 atmosphere. The mixture was heated at reflux for 35 minutes then cooled to room temperature. The thick yellow mixture was stirred at room temperature for 1 hour. The mixture was filtered and the pale orange solid was rinsed with 100 mL of the filtrate. The solid was dried in vacuo at 55° C. overnight to yield 55.5 g of pale orange solid. The solid was slurried in 275 mL of 1 N NaOH for 30 minutes. The solid was filtered off and rinsed 3 times with 50 mL portions of the filtrate. The solid was air dried in the hood over the weekend to yield 46.7 g of solid. The solid was added to 220 mL of water. Concentrated HCl (15 mL) was added to obtain pH of 1.3 and the mixture was stirred for 4 hours. The solid was filtered off and washed with 200 mL of water. The solid was dried in vacuo at 50° C. to give 37.6 g of intermediate title compound as white crystals (HPLC: 90percent with 9percent 2-naphthoic acid, 46percent yield).

Reference： [1] Patent: US2008/58423, 2008, A1, . Location in patent: Page/Page column 9
[2] Patent: US2004/6229, 2004, A1, . Location in patent: Page/Page column 15
[3] Synthetic Communications, 2011, vol. 41, # 13, p. 2017 - 2024
[4] Journal of Medicinal Chemistry, 2004, vol. 47, # 8, p. 1893 - 1899
[5] Helvetica Chimica Acta, 1938, vol. 21, p. 62,65
[6] Chemische Berichte, 1876, vol. 9, p. 1519
[7] Journal fuer Praktische Chemie (Leipzig), 1891, vol. <2> 43, p. 427
[8] Chemische Berichte, 1876, vol. 9, p. 1519
[9] Australian Journal of Chemistry, 1965, vol. 18, p. 1351 - 1364
[10] ChemMedChem, 2010, vol. 5, # 1, p. 65 - 78
[11] Patent: US3932452, 1976, A,
[12] Patent: US2003/225281, 2003, A1, . Location in patent: Page 13

5
[ 93-09-4 ]
[ 613-56-9 ]

Reference： [1] Structural Chemistry, 2012, vol. 23, # 3, p. 771 - 790,20
[2] Structural Chemistry, 2012, vol. 23, # 3, p. 771 - 790

6
[ 91-20-3 ]
[ 93-09-4 ]
[ 613-56-9 ]
[ 605-79-8 ]

Reference： [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1913, vol. 45, p. 772[2] Journal fuer Praktische Chemie (Leipzig), 1913, vol. <2> 88, p. 510
[3] Chemische Berichte, 1873, vol. 6, p. 541
[4] Chemische Berichte, 1873, vol. 6, p. 1245

7
[ 93-09-4 ]
[ 53568-17-5 ]

Reference： [1] Synthetic Communications, 2011, vol. 41, # 13, p. 2017 - 2024

8
[ 93-09-4 ]
[ 116632-14-5 ]

Reference： [1] Patent: WO2011/44394, 2011, A1,

9
[ 93-09-4 ]
[ 116632-14-5 ]
[ 90016-93-6 ]

Reference： [1] Synthetic Communications, 2012, vol. 42, # 5, p. 635 - 638

[ 93-09-4 ] Synthesis Path-Downstream 1~110

1
[ 91-57-6 ]
[ 93-09-4 ]

Reference： [1]Asian Journal of Chemistry,2012,vol. 24,p. 4445 - 4448
[2]Synthesis,2006,p. 1757 - 1759
[3]Tetrahedron Letters,2004,vol. 45,p. 8277 - 8280
[4]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1984,vol. 33,p. 2085 - 2091
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1984,p. 2284 - 2291
[5]Gazzetta Chimica Italiana,1996,vol. 126,p. 313 - 315
[6]European Journal of Organic Chemistry,2008,p. 4877 - 4880
[7]Tetrahedron Letters,1984,vol. 25,p. 4989 - 4992
[8]Tetrahedron Letters,1997,vol. 38,p. 3631 - 3634
[9]Organic Letters,2005,vol. 7,p. 4549 - 4552
[10]Synthesis,2003,p. 2289 - 2291
[11]Synlett,2005,p. 2107 - 2109
[12]Chemische Berichte,1899,vol. 32,p. 2446
[13]Organic Process Research and Development,1999,vol. 3,p. 227 - 231

2
[ 91-20-3 ]
[ 93-09-4 ]
[ 613-56-9 ]
[ 605-79-8 ]

Reference： [1]Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1913,vol. 45,p. 772
Journal fuer Praktische Chemie (Leipzig),1913,vol. <2> 88,p. 510

3
[ 93-09-4 ]
[ 53440-12-3 ]

Reference： [1]Tetrahedron,1982,vol. 38,p. 2831 - 2836
[2]Journal of the American Chemical Society,1949,vol. 71,p. 3342,3344
[3]Journal of Organic Chemistry,1959,vol. 24,p. 938,941
[4]Chemische Berichte,1891,vol. 24,p. 2358
[5]Justus Liebigs Annalen der Chemie,1891,vol. 266,p. 198
[6]Journal of Organic Chemistry,1980,vol. 45,p. 5247 - 5255
[7]Polish Journal of Chemistry,1985,vol. 59,p. 447 - 451

4
[ 93-09-4 ]
[ 1013-83-8 ]

Yield	Reaction Conditions	Operation in experiment
53.4%	With bromine; iodine; In acetic acid; for 0.5h;Heating / reflux;	To a boiling solution of 2-naphthoic acid (10.00 g, 58.14 mmol) in acetic acid (50 mL) is added dropwise bromine (3 mL) containing iodine (0.25 g). After the addition is complete, the solution is refluxed for 0.5 hr. A white precipitate forms during cooling and is isolated by filtration, washed with acetic acid and then water. The solid is triturated in methanol (100 mL) and 7.01 g (53.4percent yield) of the desired product is obtained as a white solid. m.p. 248-250° C. 1H NMR (300 MHz, CD3OD): delta 8.94 (d, J=1.8 Hz, 1H), 8.52-8.42 (m, 3H), 8.27 (dd, J=1.8, 7.5 Hz, 1H), 7.79 (t, J=8.4 Hz, 1H).
46%	With bromine;iodine; In acetic acid; for 0.583333h;Heating / reflux;	Preparation 3 [0106] Preparation of 6-Iodo-1-methoxy-naphthalene. [CHEMMOL-00022] [0107] Preparation of 5-Bromo-2-naphthalenecarboxylic acid. [0108] 2-Naphthoic acid (50;0 g, 0.290 mol), glacial acetic acid (250 mL), bromine (15 mL, 0.291 mol) and iodine (1.3 g, 0.005 mol) were combined in a flask under N2 atmosphere. The mixture was heated at reflux for 35 minutes then cooled to room temperature. The thick yellow mixture was stirred at room temperature for 1 hour. The mixture was filtered and the pale orange solid was rinsed with 100 mL of the filtrate. The solid was dried in vacuo at 55° C. overnight to yield 55.5 g of pale orange solid. The solid was slurried in 275 mL of 1 N NaOH for 30 minutes. The solid was filtered off and rinsed 3 times with 50 mL portions of the filtrate. The solid was air dried in the hood over the weekend to yield 46.7 g of solid. The solid was added to 220 mL of water. Concentrated HCl (15 mL) was added to obtain pH of 1.3 and the mixture was stirred for 4 hours. The solid was filtered off and washed with 200 mL of water. The solid was dried in vacuo at 50° C. to give 37.6 g of intermediate title compound as white crystals (HPLC: 90percent with 9percent 2-naphthoic acid, 46percent yield).
76 g (75%)	With I2; bromine; acetic acid;	A. 5-Bromo-2-Naphthoic Acid A 75 g (0.44 mole) portion of 2-naphthoic acid, 375 ml of acetic acid, 22.5 ml of Br2 (70 g, 0.44 mole) and 1.9 g (0.015 mole) of I2 were placed in a 1 l. 3-necked flask and refluxed with stirring for 0.6 hours. The reaction mixture was cooled to 25° and filtered. The cream solid was washed with small portions of the filtrate, air dried and dried to a constant weight at 60° to give 76 g (75percent) of a light tan-cream solid, m.p. 224°-233° dec. The crude product was slurried with 375 ml of 1 N NaOH for 0.5 hours and filtered.

With bromine;iodine; In acetic acid; at 20 - 116℃; for 1.58333h;Heating / reflux;

2-Naphthoic acid (50.0 g, 0.290 mol), glacial acetic acid (250 mL), bromine (15 mL, 0.291 mol) and iodine (1.3 g, 0.005 mol) were combined in a flask under N2 atmosphere. The mixture was heated at reflux for 35 minutes then cooled to room temperature. The thick yellow mixture was stirred at room temperature for 1 hour. The mixture was filtered and the pale orange solid was rinsed with ?100 mL of the filtrate. The solid was dried in vacuo at 55 C. overnight to yield 55.5 g of pale orange solid. The solid was slurried in 275 mL of 1 N NaOH for 30 minutes. The solid was filtered off and rinsed 3 times with 50 mL portions of the filtrate. The solid was air dried in the hood over the weekend to yield 46.7 g of solid. The solid was added to 220 mL of water. Concentrated HCl (15 mL) was added to obtain pH of 1.3 and the mixture was stirred for 4 hours. The solid was filtered off and washed with 200 mL of water. The solid was dried in vacuo at 50 C. to give 37.6 g of intermediate title compound as white crystals (HPLC: 90percent with 9percent 2-naphthoic acid, 46percent yield).

Reference： [1]Patent: US2008/58423,2008,A1 .Location in patent: Page/Page column 9
[2]Patent: US2004/6229,2004,A1 .Location in patent: Page/Page column 15
[3]Synthetic Communications,2011,vol. 41,p. 2017 - 2024
[4]Journal of Medicinal Chemistry,2004,vol. 47,p. 1893 - 1899
[5]Helvetica Chimica Acta,1938,vol. 21,p. 62,65
[6]Chemische Berichte,1876,vol. 9,p. 1519
[7]Chemische Berichte,1876,vol. 9,p. 1519
[8]Australian Journal of Chemistry,1965,vol. 18,p. 1351 - 1364
[9]ChemMedChem,2010,vol. 5,p. 65 - 78
[10]Patent: US3932452,1976,A
[11]Patent: US2003/225281,2003,A1 .Location in patent: Page 13

5
[ 1592-38-7 ]
[ 93-09-4 ]

Yield	Reaction Conditions	Operation in experiment
99.9%	With silica-supported Jones reagent In dichloromethane for 0.035h;
97%	With N-Bromosuccinimide; oxygen In acetonitrile at 20℃; for 10h; Irradiation;
94%	With hydrogen bromide; oxygen In acetonitrile for 10h; Irradiation;

90%	With dichloro(1,5-cyclooctadiene)ruthenium(II); C₃₀H₃₀N₃P₂⁽¹⁺⁾*Cl^(1-); potassium hydroxide In toluene at 120℃; for 24h; Inert atmosphere; Schlenk technique;
86%	With tert.-butylhydroperoxide; sodium chloride; sodium hydroxide In water monomer at 70℃; Sealed tube; Green chemistry;
81%	With tripotassium phosphate tribasic; carbon dioxide; CrH₆Mo₆O₂₄^(3-)3H₃N3H⁽¹⁺⁾ In dimethyl sulfoxide at 80℃; for 24h; Green chemistry;
81%	With sodium trifluoro-methanesulfinate In acetonitrile at 25℃; for 12h; Irradiation; Sealed tube;
80%	Stage #1: 2-Naphthalenemethanol With Ru(η(2)-2-(2'-pyridyl)phenyl)Cl(CO)(PPh3)2; potassium hydroxide In toluene at 120℃; for 6h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In water monomer
76%	With oxygen at 120℃; for 16h; Green chemistry;
75%	With potassium hydroxide In toluene at 120℃; for 12h;	2.3 General procedure for the dehydrogenation of benzylic alcohols General procedure: Benzylic alcohols (1.0mmol), solid 1a (0.2-2mol %), KOH (2-4 equiv.) and 1.5mL toluene were charged sequentially in a 25mL tube with a magnetic bar. The reaction tube was stirred at 120°C for 12-48h attached with an open bubbler. After the certain reaction time, water (5mL) was added, and the mixture was extracted with diethyl ether (3×5mL). Then the aqueous phase was acidified with HCl (6M) and further extracted with ethyl acetate (3×10mL). The combined ethyl acetate solution was washed with brine (15mL), dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressure, the pure acids was obtained and weighted for calculating the yield.
73%	With manganese(II) bromide; anhydrous silver carbonate; potassium hydroxide In 1,3,5-trimethyl-benzene at 50 - 165℃; for 8h; Schlenk technique; Inert atmosphere;
73%	Stage #1: 2-Naphthalenemethanol With ((CH₃C₆H₄CH(CH₃)2)RuI(C₆H₄NC₃H₂NCH₃)); potassium hydroxide In 1,3-dimethylbenzene for 6h; Schlenk technique; Reflux; Stage #2: With hydrogenchloride In water monomer; 1,3-dimethylbenzene Schlenk technique;
71%	With potassium hydroxide In 1,3,5-trimethyl-benzene at 160℃; for 24h; Inert atmosphere;	2.4. General procedure for dehydrogenativeoxidation of alcohols General procedure: 1 mmol of alcohol, 2 mmol(112 mg)potassium hydroxide and 30 mg of prepared catalyst(MnFe-S-Ag) were mixed in areaction flask and 2 mL mesitylene was also added. The mixture was stirred for24 hours at 160°C under argon atmosphere.Progress of reaction was monitored using TLC analysis. When the reactionwas considered complete, catalyst was collected with a permanent magnet. Thensolvent was evaporated under reduced pressure. Water (10 mL) was added to theresulting mixture to dissolve salts. The starting material was removed toorganic layer, with extraction of the reaction mixture with EtOAc(3×10 mL).Subsequently, the aqueous layer was acidified to pH 5-6 with a 20% HClsolution(2-5 mL). The target acid was generated as a white to yellowprecipitate. Then it was extracted to EtOAc(3×10 mL) and the crudeproduct was obtained after evaporation of the organic solvent and it wasfurther purified by recrystallization if necessary.
70%	With carbon tetrabromide; oxygen; triphenylphosphine In acetonitrile for 10h; fluorescent irradiation;
70%	With potassium hydroxide; zinc oxide In 1,3,5-trimethyl-benzene at 164℃; for 18h; Inert atmosphere; Schlenk technique;
65%	Stage #1: 2-Naphthalenemethanol With C₁₂H₁₄ClN₂Ru⁽¹⁺⁾*F₆P^(1-); potassium hydroxide In toluene at 110℃; for 6h; Inert atmosphere; Stage #2: With hydrogenchloride In water monomer
0.82 g	With potassium hydroxide at 210℃;
0.82 g	With potassium hydroxide at 210℃; reaction with powdered KOH under melting condition, hydrogen das evolution during the reaction;
	With E_. coli perisplasmic aldehyde oxidase; F_. graminearum galactose oxidase; catalase In aq. phosphate buffer; acetonitrile at 37℃; for 10h; Enzymatic reaction;
88 %Chromat.	With C₁₉H₂₆IrN₃O₂⁽²⁺⁾*2CF₃O₃S^(1-) In 1,4-dioxane; water monomer for 20h; Reflux;
	Multi-step reaction with 2 steps 1: chloro(η⁶-p-cymene)[2-(2,6-diisopropylphenyl)-5-(1,3-diisopropyl-2,4,6-trioxohexahydropyrimidin-5-yl-κC⁵)imidazo[1,5-a]pyridin-3-ylidene-κC³]ruthenium(II); potassium hydroxide / dichloromethane; o-dimethylbenzene / 150 °C / Schlenk technique 2: hydrogenchloride / water monomer / pH 2 / Schlenk technique
	With ((CH₃C₆H₄CH(CH₃)2)RuI(C₆H₄NC₃H₂NCH₃)); potassium hydroxide In 1,3-dimethylbenzene at 145℃; for 12h; Schlenk technique;	2.4.1. A typical reaction under the optimized reaction condition General procedure: To a 25mL Schlenk flask, an NHC-Ru complex (one of [Ru-1]-[Ru-7], 1.56 μmol), an alcohol (25mmol), KOH (1.68g, 30mmol), a stirring bar, and m-xylene (3.0mL) were added. The flask was equipped with a reflux condenser, and the reaction mixture was stirred at a refluxing temperature in open air. After the assigned reaction period, the flask was cooled to room temperature. Water (10mL) and ethyl acetate (20mL) were added, and the two layers were separated. The organic layer was collected, and the aqueous layer was further extracted with ethyl acetate (3× 20mL). Subsequently, the organic layers were combined, dried over Na2SO4, concentrated via a rotary evaporator, dried with a vacuum pump to afford the unreacted alcohol, which was weighed to obtain its yield. Afterwards, 3N HCl (around 12mL) was added to the aqueous layer, which was extracted with ethyl acetate (3× 20mL). The organic layers were combined, dried over Na2SO4, concentrated and dried to afford the desired carboxylic acid, which was weighed to determine its yield.

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[18]Berner, Endre [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 8, p. 547 - 549]
[19]McKenna, Shane M.; Leimkühler, Silke; Herter, Susanne; Turner, Nicholas J.; Carnell, Andrew J. [Green Chemistry, 2015, vol. 17, # 6, p. 3271 - 3275]
[20]Fujita, Ken-Ichi; Tamura, Ryuichi; Tanaka, Yuhi; Yoshida, Masato; Onoda, Mitsuki; Yamaguchi, Ryohei [ACS Catalysis, 2017, vol. 7, # 10, p. 7226 - 7230]
[21]Benaissa, Idir; Gajda, Katarzyna; Vendier, Laure; Lugan, Noël; Kajetanowicz, Anna; Grela, Karol; Michelet, Véronique; César, Vincent; Bastin, Stéphanie [Organometallics, 2021, vol. 40, # 18, p. 3223 - 3234]
[22]Chen, Cheng; Cheng, Hua; Verpoort, Francis; Wang, Zhi-Qin; Wu, Zhe; Yuan, Ye; Zheng, Zhong-Hui [Applied Catalysis A: General, 2022, vol. 630]

6
[ 201230-82-2 ]
[ 3857-83-8 ]
[ 93-09-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium acetate In dimethyl sulfoxide at 60℃; for 4h;

Reference： [1]Cacchi, Sandro; Lupi, Alessandro [Tetrahedron Letters, 1992, vol. 33, # 27, p. 3939 - 3942]

7
[ 201230-82-2 ]
[ 612-55-5 ]
[ 93-09-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With water; potassium carbonate; In acetonitrile; at 100℃; under 3750.38 Torr; for 0.0161111h;	General procedure: A 25 mM solution of iodobenzene (5a) and K2CO3 (2 equiv) in H2O/CH3CN (2:1) was pumped at a flow rate of 1.0 mL/min(contact time: 58 s) through a Phoenix flow reactor systemequipped with two cartridges of 4 (total 500 mg; 0.084 mmolPd). Flow hydroxycarbonylation with CO gas introduced from agas module (10 mL/min) was conducted at 100 C and a systempressure of 5 bar. The resulting solution was collected for 50min (50 mL) and the solvent was removed by evaporation. 2 Naq HCl (10 mL) was added and the resulting solid was collectedby filtration, washed with H2O (3 × 10 mL), and dried undervacuum to give benzoic acid (9a) as a white solid without anyfurther purification.Yield: 125 mg (82%); mp 122 C; 1H NMR(400 MHz, DMSO-d6): delta = 12.96 (br s, 1 H, COOH), 7.93 (d, J = 7.2Hz, 2 H, PhH-2 and PhH-6), 7.62 (t, J = 7.2 Hz, 1 H, PhH-4), 7.49 (t, J =7.2 Hz, 2 H, PhH-3 and PhH-5); 13C NMR (101 MHz, DMSO-d6): delta = 167.32 (COOH), 132.87 (Ph), 130.76 (Ph), 129.26 (Ph),128.57 (Ph); ESI-TOF-MS (neg.): m/z = 121 [M - H]-.
53%	With water; palladium diacetate; triethylamine; triphenylphosphine; In 1,4-dioxane; at 110℃; under 11251.1 Torr; for 2h;Flow reactor;	General procedure: For a typical reaction, a Vapourtec 2R+ Series was used as the platform with a Vapourtec Gas/Liquid Membrane Reactor to load the carbon monoxide. The HPLC pump were both set at 0.125 mL/min, temperature of the reactor at 110 C, pressure of CO at 15 bar with a back pressure regulator of 250 psi (17.24 bar). The system was left running for 2 h to reach steady state after which time the flow streams were switched to pass from the loops where the substrates and catalysts were loaded. The first loop (5 mL) was filled with a solution of palladium acetate (20 mg, 0.08 mmol), triphenylphosphine (48 mg, 0.168 mmol) in 6 mL of 1,4-dioxane while the second loop (5 mL) was filled with a solution made from the ortho-substituted iodoarene substrate (1.68 mmol), triethylamine (0.272 g, 0.374 mL, 2.69 mmol) and water (0.505 g, 28 mmol) in 5.8 mL of 1,4-dioxane. An Omnifit column filled with 1.71 cm3 (r = 0.33 cm, h = 5.00 cm) of cotton was positioned just before the back pressure regulator to trap any particulate matter formed to avoid blocking of the back pressure regulator. After the substrates were passed through the system, the outlet of the flow stream was directed into a receptacle where the excess carbon monoxide gas was vented off in the fume cupboard. The reaction mixture was then evaporated to dryness, ethyl acetate (25 mL) and sodium carbonate solution (2 M, 10 mL) were added and transferred to a separating funnel. After collecting the aqueous layer, the organic layer was extracted with sodium carbonate solution (2 M, 2 × 10 mL). The combined aqueous layers were acidified by the addition of 2 M HCl solution which was then extracted with ethyl acetate (3 x 25 mL). The organic layer was dried over sodium sulfate, and the solvent evaporated under vacuum to give the crude product as a solid. The crude product was then recrystallised from the appropriate solvent.

Reference： [1]Synlett,2019,vol. 30,p. 961 - 966
[2]Journal of Organometallic Chemistry,1988,vol. 358,p. 563 - 566
[3]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 1503 - 1511
[4]ChemCatChem,2018,vol. 10,p. 1089 - 1095

8
[ 883-21-6 ]
[ 3299-82-9 ]
[ 53440-12-3 ]
[ 93-09-4 ]

Reference： [1]Tetrahedron,1982,vol. 38,p. 2831 - 2836

9
[ 76373-16-5 ]
[ 18531-96-9 ]
[ 5978-70-1 ]
[ 93-09-4 ]

Reference： [1]Chemistry Letters,1980,p. 1027 - 1030

10
[ 74-88-4 ]
[ 93-09-4 ]
[ 70335-56-7 ]
[ 53440-12-3 ]

Reference： [1]Tetrahedron,1982,vol. 38,p. 2831 - 2836

11
[ 67-56-1 ]
[ 93-09-4 ]
[ 67878-76-6 ]

Reference： [1]Journal of Fluorine Chemistry,1988,vol. 38,p. 139 - 152

12
[ 6638-79-5 ]
[ 93-09-4 ]
[ 113443-62-2 ]

Yield	Reaction Conditions	Operation in experiment
93%		General procedure: A. To a mixture of benzoic acid (50 mg, 0.41 mmol, 1 equiv), PPh3 (160 mg, 0.61 mmol, 1.5 equiv) and NBS (108.5 mg, 0.61 mmol, 1.5 equiv), CH2Cl2 (2 ml) was added and the reaction was stirred at 0 C for 15 min. The reaction was brought to room temperature and N,O-dimethylhydroxylamine hydrochloride (59.5 mg, 0.61 mmol, 1.5 equiv) and Et3N (45.5 mg, 63 mul, 0.45 mmol, 1.1 equiv) were added and reaction was stirred for 1 h at room temperature. The reaction mixture was quenched with aqueous sodium bicarbonate solution and diluted with CH2Cl2. The bicarbonate washings were again extracted with CH2Cl2 and the combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. Column chromatography was performed using EtOAc/Petroleum ether (1:5).
90%	With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃; for 12h;	N-Methoxy-N-methyl-2-naphthamide was prepared in 90% yield according to the Example 1 , Step A substituting 6-bromopicolinic acid for 2-naphthoic acid.
58%	With 1,1'-carbonyldiimidazole; In DMF (N,N-dimethyl-formamide); at 20℃; for 48h;	Naphthalene-2-carboxylic acid methoxy-methyl-amide In a 250 mL round-bottom flask equipped with a stir bar, was charged 2-napthoic acid (11.23 g, 65.22 mmol), N, N'-carbonyldiimidazole (15. 88 g, 47.8 mmol), N, [O-] dimethylhydroxylamine [HC1] (10.27 g, 104.4 mmol) and DMF (100 mL). The resulting solution was stirred at room temperature for 48 h. The reaction was then diluted by 200 mL EtOAc and washed by 200 mL [10%] HC1. The aqueous was extracted by 100 mL EtOAc and the combined organics washed with saturated sodium bicarbonate solution followed by brine. The organic layer was separated, dried by [NA2SO4,] and concentrated in vacuo to give 9.29 g of crude product. This was purified by flash chromatography (Si02, 2: [1-1] : 1 Hexane: EtOAc) to give compound 1 (8.2 g, [58%)] as a colorless oil. MS (ES+) : 215 (M+H) +.

Reference： [1]Synthetic Communications,2020,vol. 50,p. 1622 - 1632
[2]Journal of the American Chemical Society,2019,vol. 141,p. 4738 - 4748
[3]Patent: WO2015/140133,2015,A1 .Location in patent: Page/Page column 135
[4]Angewandte Chemie - International Edition,2015,vol. 54,p. 14017 - 14021
Angew. Chem.,2015,vol. 127,p. 14223 - 14227,5
[5]Patent: WO2003/99808,2003,A1 .Location in patent: Page 52
[6]Journal of Organic Chemistry,1991,vol. 56,p. 3283 - 3286

13
[ 49721-45-1 ]
[ 93-09-4 ]
[ 127820-11-5 ]

Reference： [1]Journal of Medicinal Chemistry,1990,vol. 33,p. 2073 - 2080

14
[ 93-09-4 ]
[ 2243-82-5 ]

Yield	Reaction Conditions	Operation in experiment
97%		Unless otherwise specified, carboxylic acid (0.542 mmol), TCT (0.0400 g, 0.216 mmol) and K2CO3 (0.2247 g, 1.626 mmol) were mixed together and hand ground for one minute using porcelain mortar and pestle. After addition of ammonium thiocyanate (0.0495 g, 0.650 mmol), the mixture was ground manually for further five minute. During the grinding, THF (calculated to be less than 1 L/mg of solids) was added to aid homogeneous mixing. The crude material was then purified by short column chromatography (column diameter 1.5 cm, packed with 3-4 g silica gel ) using 40-50percent ethyl acetate/hexane as an eluent.
	With ammonium hydroxide;N,N-dimethyl-formamide; In oxalyl dichloride; hexane; water;	(1) PREPARATION OF NAPHTHALENE-2-CARBOXYLIC ACID AMIDE To a solution of 2-naphthoic acid (25 g, 0.145 mol) in MC (200 ml), oxalyl chloride (38 ml, 0.4356 mol) and a catalytic amount of DMF were added and stirred at room temperature for 2 hrs. After the solvent was evaporated, the crude acyl chloride was diluted with MC (200 ml), to which a solution of ammonium hydroxide in water (160 ml) was dropwise added at an ice bath temperature. After stirring for 1 hr, the precipitated product was collected by suction filtration, triturated in hexane and dried to obtain the title compound, which was used next step without further purification.
	With ammonia; at 195℃; for 0.5h;	General procedure: Into a 1L open reactor was added 500g of carboxylic acid raw material (chemically pure) and stirring was turned on (600 r/min) from the reactorThe bottom is continuously fed with ammonia gas (chemical purity, water content of 5.1percent by weight, flow rate of 100 g/min) to the carboxylic acid feed. After the reaction was allowed to proceed for TC hours at the reaction temperature TA, ammonia gas flow was stopped. The contents of the reactor were sampled and subjected to nuclear magnetic proton and elemental analysis to characterize the amide intermediate. Specific reaction conditions and characterization results are shown in Table A-1, Table A-2, Table A-3, Table A-4, Table A-5 and Table A-6. These characterization results show that the amide intermediates obtained have an extremely high purity (above 99percent).In this embodiment, the ammonia gas can be directly replaced with waste ammonia gas (from Yangzi Petrochemical Plant, containing approximately50wtpercent of ammonia gas, the rest were toluene, oxygen, nitrogen, steam, carbon monoxide, and carbon dioxide, and the flow rate of this waste ammonia was 130g/min).

Reference： [1]Heterocycles,2006,vol. 68,p. 1149 - 1162
[2]Tetrahedron Letters,2018,vol. 59,p. 3571 - 3573
[3]Bioscience, Biotechnology and Biochemistry,2001,vol. 65,p. 1761 - 1765
[4]Synthesis,1983,p. 142 - 143
[5]Journal of Medicinal Chemistry,2006,vol. 49,p. 684 - 692
[6]Justus Liebigs Annalen der Chemie,1876,vol. 180,p. 305
Chemische Berichte,1875,vol. 8,p. 1278
[7]Patent: US2004/53331,2004,A1
[8]Patent: WO2012/159666,2012,A1
[9]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1324 - 1332
[10]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1424 - 1427
[11]Patent: CN104557357,2018,B .Location in patent: Paragraph 0135; 0136; 0137; 0139

15
[ 91-57-6 ]
[ 7469-77-4 ]
[ 93-09-4 ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,1996,vol. 60,p. 769 - 772

16
[ 71989-31-6 ]
[ 73724-45-5 ]
[ 135273-01-7 ]
[ 93-09-4 ]
(5S,8R,13R,15aS)-5-Hydroxymethyl-8-[(naphthalene-2-carbonyl)-amino]-4,7,15-trioxo-tetradecahydro-10,11-dithia-3a,6,14-triaza-cyclopentacyclotetradecene-13-carboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 3359 - 3368

17
[ 20248-86-6 ]
[ 93-09-4 ]
[ 215320-90-4 ]

Yield	Reaction Conditions	Operation in experiment
39%	With potassium hydroxide In N,N,N,N,N,N-hexamethylphosphoric triamide at 25℃; for 24h;

Reference： [1]McGimpsey; Samaniego; Chen; Wang [Journal of Physical Chemistry A, 1998, vol. 102, # 45, p. 8679 - 8689]

18
[ 93-09-4 ]
aqueous KOH-solution [ No CAS ]
sodium amalgam [ No CAS ]
[ 53440-12-3 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1891,vol. 266,p. 198

19
[ 15719-64-9 ]
[ 93-09-4 ]
aqueous solution [ No CAS ]
sodium-amalgam [ No CAS ]
[ 53440-12-3 ]

Reference： [1]Journal of the American Chemical Society,1949,vol. 71,p. 3342,3344

20
[ 71-41-0 ]
[ 93-09-4 ]
sodium [ No CAS ]
[ 53440-12-3 ]

Reference： [1]Chemische Berichte,1891,vol. 24,p. 2358

21
[ 93-09-4 ]
aqueous KOH-solution [ No CAS ]
sodium amalgam [ No CAS ]
[ 3299-82-9 ]
[ 3408-30-8 ]
[ 53440-12-3 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1891,vol. 266,p. 192

22
[ 613-46-7 ]
[ 64-17-5 ]
sodium [ No CAS ]
[ 2243-82-5 ]
[ 74-90-8 ]
[ 7664-41-7 ]
[ 93-09-4 ]

Reference： [1]Chemische Berichte,1887,vol. 20,p. 1711

23
[ 3029-32-1 ]
potassium hydroxide [ No CAS ]
[ 91-20-3 ]
[ 93-09-4 ]

Reference： [1]Journal of the Chemical Society,1912,vol. 101,p. 2206,2208

24
[ 613-56-9 ]
soda lime [ No CAS ]
[ 91-20-3 ]
[ 93-09-4 ]

Reference： [1]Chemische Berichte,1873,vol. 6,p. 1245

25
[ 861546-41-0 ]
sodium amide [ No CAS ]
[ 108-88-3 ]
[ 2243-82-5 ]
[ 91-20-3 ]
[ 926-04-5 ]
[ 93-09-4 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1910,vol. 150,p. 1176

26
[ 861546-41-0 ]
sodium amide [ No CAS ]
[ 71-43-2 ]
[ 2243-82-5 ]
[ 91-20-3 ]
[ 926-04-5 ]
[ 93-09-4 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1910,vol. 150,p. 1176

27
[ 65473-13-4 ]
[ 93-09-4 ]
naphthalene-2-carboxylic acid methyl-naphthalen-1-ylmethyl-amide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,1997,vol. 7,p. 98 - 108

28
[ 93-09-4 ]
[ 53440-12-3 ]
[ 1131-63-1 ]

Reference： [1]Biodegradation,2000,vol. 11,p. 117 - 124

29
[ 26487-67-2 ]
[ 93-09-4 ]
naphthalene-2-carboxylic acid 2-azepan-1-yl-ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 3244 - 3253

30
[ 131570-56-4 ]
N-α-(9-fluoromethoxycarbonyl)-L-4-tert-butoxycarbonylaminophenylalanine [ No CAS ]
[(S)-4-({Amino-[(E)-2,2,5,7,8-pentamethyl-chroman-6-sulfonylimino]-methyl}-amino)-1-hydroxymethyl-butyl]-carbamic acid 9H-fluoren-9-ylmethyl ester [ No CAS ]
[ 93-09-4 ]
2-fluoro-5-nitrobenzoic acid [ No CAS ]
Naphthalene-2-carboxylic acid [(7S,10S,13S)-13-amino-10-(4-amino-benzyl)-7-(3-guanidino-propyl)-9,12,16-trioxo-7,8,9,10,11,12,13,14,15,16-decahydro-6H-5-oxa-8,11,15-triaza-benzocyclotetradecen-2-yl]-amide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3430 - 3439

31
[ 98-80-6 ]
[ 93-09-4 ]
[ 644-13-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With 2,2-dimethylpropanoic anhydride; triphenylphosphine In tetrahydrofuran; water at 60℃; for 16h;

Reference： [1]Goossen, Lukas J.; Ghosh, Keya [European Journal of Organic Chemistry, 2002, # 19, p. 3254 - 3267]

32
[ 67436-13-9 ]
[ 143824-78-6 ]
[ 541-88-8 ]
[ 93-09-4 ]
(S)-N-α-Fmoc-N-ε-Boc-lysinal [ No CAS ]
(S)-2-{(R)-6-(4-Amino-butyl)-9-[(naphthalene-2-carbonyl)-amino]-3,8-dioxo-[1,4,7]thiadiazecan-4-yl}-3-(1H-indol-3-yl)-propionic acid [ No CAS ]
Naphthalene-2-carboxylic acid {(R)-6-(4-amino-butyl)-4-[(S)-1-carbamoyl-2-(1H-indol-3-yl)-ethyl]-3,8-dioxo-[1,4,7]thiadiazecan-9-yl}-amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 11046 - 11055

33
[ 119072-55-8 ]
[ 26260-02-6 ]
[ 177911-87-4 ]
[ 93-09-4 ]
2-[[tert-butylcarbamoyl-(2-iodo-phenyl)-methyl]-(naphthalene-2-carbonyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 1697 - 1701

34
[ 874-89-5 ]
[ 73918-56-6 ]
[ 31708-25-5 ]
[ 93-09-4 ]
naphthalene-2-carboxylic acid [2-(4-bromo-phenyl)-ethyl]-[4-(4-cyano-benzyl)-4H-[1,2,4]triazol-3-ylmethyl]-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 5407 - 5411

35
[ 124-38-9 ]
[ 627906-96-1 ]
[ 93-09-4 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 8706 - 8707
[2]Chemical Communications,2012,vol. 48,p. 6292 - 6294

36
[ 1592-38-7 ]
[ 66-99-9 ]
[ 93-09-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 75% 2: 9%	With tert-butyl 1-hydroxy-2-methyl-6-trifluoromethyl-1H-indole-3-carboxylate; oxygen; copper chloride (I) In N,N-dimethyl-formamide at 50℃; for 12h;	2.2 General procedure for aerobic oxidation of allylic and benzylic alcohols General procedure: To a 10 mL Schlenk tube, NHI-1 (0.2 mmol, 63 mg) and CuCl (0.2 mmol, 19.6 mg) and DMF (2 mL) were added and stirred at 50 °C for about 30 min to form a dark red solution. Alcohol 11 (2 mmol) was added, the mixture was left to stir at 50 °C under an oxygen balloon (1 atm). The reaction progress was monitored by TLC or GC. After completion, the mixture was allowed to cool to room temperature, quenched with 1M HCl and diluted with H2O (50 mL), extracted with EtOAc (EA) (10 mL × 3), the combined organic layer was washed with brine and dried over MgSO4, the crude was purified by flash column chromatography (EtOAc : hexane = 1 : 10 to 1: 3) to afford ketone or aldehyde 12.
1: 51% 2: 41%	With 2.9-dimethyl-1,10-phenanthroline; oxygen; Sodium hydrogenocarbonate In lithium hydroxide monohydrate at 100℃; for 24h;
	With oxygen; HNO₃ In 1,4-dioxane; lithium hydroxide monohydrate at 90℃; for 5h; chemoselective reaction;

1: 13 %Chromat. 2: 41.9 %Chromat.	With oxygen; palladium diacetate In neat (no solvent) at 150℃; for 15h;
1: 70 %Chromat. 2: 3 %Chromat.	With sulfuric acid; dihydrogen peroxide; C₂₃H₃₀CuN₂O₃ In acetonitrile at 70℃; for 2h;	4.6 Catalytic oxidation of alcohols General procedure: A typical procedure using complex 3 as catalyst and H2O2 as oxidant is as follows. An alcohol substrate (1.0mmol), complex 3 (2.0mol%), H2SO4 (1.0mmol) and H2O2 (8.0mmol) were mixed in 2.0mL CH3CN. The solution was stirred at 70°C for 2h. The reaction yields were analyzed by GC.

Reference： [1]Shen, Shu-Su; Kartika, Vita; Tan, Ying Shan; Webster, Richard D.; Narasaka, Koichi [Tetrahedron Letters, 2012, vol. 53, # 8, p. 986 - 990]
[2]Li, Huanrong; Guan, Bingtao; Wang, Wenjin; Xing, Dong; Fang, Zhao; Wan, Xiaobing; Yang, Liping; Shi, Zhangjie [Tetrahedron, 2007, vol. 63, # 35, p. 8430 - 8434]
[3]Location in patent: experimental part Kuang, Yongbo; Islam, Nazrul M.; Nabae, Yuta; Hayakawa, Teruaki; Kakimoto, Masa-Aki [Angewandte Chemie - International Edition, 2010, vol. 49, # 2, p. 436 - 440]
[4]Tiburcio, Estefanía; Greco, Rossella; Mon, Marta; Ballesteros-Soberanas, Jordi; Ferrando-Soria, Jesús; López-Haro, Miguel; Hernández-Garrido, Juan Carlos; Oliver-Meseguer, Judit; Marini, Carlo; Boronat, Mercedes; Armentano, Donatella; Leyva-Pérez, Antonio; Pardo, Emilio [Journal of the American Chemical Society, 2021, vol. 143, # 6, p. 2581 - 2592]
[5]Han, Zhangang; Hao, Zhiqiang; Lin, Jin; Lu, Guo-Liang; Ma, Zhihong; Zhang, Junhua; Zhang, Xiaoying [Polyhedron, 2022, vol. 221]

37
[ 93-09-4 ]
[ 835-58-5 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1974,vol. 10,p. 1715 - 1720
Zhurnal Organicheskoi Khimii,1974,vol. 10,p. 1698 - 1704

38
[ 93-09-4 ]
N^a-Fmoc-His-D-Phe-Arg-Trp-resin conjugate [ No CAS ]
[ 2243-82-5 ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 3822 - 3839

39
[ 93-09-4 ]
permanganate [ No CAS ]
[ 1013-83-8 ]

Reference： [1]Journal of Fluorine Chemistry,1988,vol. 38,p. 139 - 152

40
[ 532-02-5 ]
[ 93-09-4 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1888,vol. <2> 38,p. 161
 Journal fuer Praktische Chemie (Leipzig),1891,vol. 43,p. 432
[2]Justus Liebigs Annalen der Chemie,1876,vol. 180,p. 305
 Chemische Berichte,1875,vol. 8,p. 1278
[3]Journal of the American Chemical Society,1921,vol. 43,p. 901
[4]Justus Liebigs Annalen der Chemie,1876,vol. 180,p. 305
 Chemische Berichte,1875,vol. 8,p. 1278
[5]Journal of the American Chemical Society,1916,vol. 38,p. 416

41
O-dimethylhydroxylamine hydrochloride [ No CAS ]
[ 93-09-4 ]
[ 113443-62-2 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; triethylamine; In dichloromethane;	a) Preparation of 2-Naphthoic-N-methoxy-N-methyl amide At 0 C., SOCl2 (5 mL, 68.5 mmol) was added very slowly to a stirred solution of 2-naphthoic acid (10 g, 58.0 mmol) in CH2Cl2 (110 mL) and Et3N (28.3 mL, 203.0 mmol). The solution became dark and homogeneous. After stirring at room temprature for 40 min., N, O-dimethylhydroxylamine hydrochloride (5.85, 60 mmol) was added. After the reaction was stirred for 2 hours, it was quenched with water, then extracted with CH2Cl2 (3). The organic layer was washed with saturated Na2CO3 (3), dried (Na2SO4), concentrated to afford the title compound. MS(ES) m/e 216 [M+H]+.

Reference： [1]Patent: US6548503,2003,B1

42
[ 93-09-4 ]
[ 67878-76-6 ]

Yield	Reaction Conditions	Operation in experiment
38%	With sodium hydroxide; sulfuric acid; bromine; iodine; In methanol; acetic acid;	Step (1) Preparation of Methyl 5-Bromo-2-naphthoate To a boiling solution of 2-naphthoic acid (200 g, 1.16 mol) in acetic acid (1000 mL) was added dropwise bromine (60 mL, 2.2 mol) containing 5.0 g of iodine. After the addition was complete, the solution was refluxed for an additional 0.5 hour. After cooling the precipitated product was isolated by filtration, washed with acetic acid and water. The crude acid was treated with hot 1N sodium hydroxide solution (1000 mL). The resulting suspension was filtered to give the sodium salt of the carboxylic acid (107 g). On cooling the filtrate furnished an additional material (43 g, total 150 g). This was suspended in methanol (1L) and concentrated sulfuric acid (68 mL) was added gradually. This suspension was refluxed for 18 hours. After cooling, the resulting solution was evaporated to dryness in vacuo and the residue partitioned between methylene chloride and water. The aqueous layer was extracted with methylene chloride and the combined organic layers were washed with saturated sodium bicarbonate solution and with water. This was dried (MgSO4) and evaporated in vacuo to give the crude title compound (116.5 g, 38%) as an oil which crystallized slowly on standing to an off-white solid, m.p. 65-68 C.
38%	With sodium hydroxide; sulfuric acid; bromine; iodine; In methanol; acetic acid;	Step (1) Preparation of Methyl 5-Bromo-2-naphthoate To a boiling solution of 2-naphthoic acid (200 g, 1.16 mol) in acetic acid (1000 mL) was added dropwise bromine (60 mL, 2.2 mol) containing 5.0 g of iodine. After the addition was complete, the solution was refluxed for an additional 0.5 hour. After cooling the precipitated product was isolated by filtration, washed with acetic acid and water. The crude acid was treated with hot 1N sodium hydroxide solution (1000 mL). The resulting suspension was filtered to give the sodium salt of the carboxylic acid (107 g). On cooling the filtrate furnished an additional material (43 g, total 150 g). This was suspended in methanol (1 L) and concentrated sulfuric acid (68 mL) was added gradually. This suspension was refluxed for 18 hours. After cooling, the resulting solution was evaporated to dryness in vacuo and the residue partitioned between methylene chloride and water. The aqueous layer was extracted with methylene chloride and the combined organic layers were washed with saturated sodium bicarbonate solution and with water. This was dried (MgSO4) and evaporated in vacuo to give the crude title compound (116.5 g, 38%) as an oil which crystallized slowly on standing to an off-white solid, m.p. 65-68 C.

Reference： [1]Patent: US4897405,1990,A
[2]Patent: US4966975,1990,A

43
[ 1201-74-7 ]
[ 93-09-4 ]
[ 1155860-29-9 ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 1335 - 1339

44
[ 82409-02-7 ]
[ 93-09-4 ]
[ 1138038-67-1 ]

Reference： [1]Chemical Communications,2009,p. 668 - 670

45
[ 181633-42-1 ]
[ 93-09-4 ]
[ 224796-63-8 ]

Yield	Reaction Conditions	Operation in experiment
10%	With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 60℃; for 8h;	8 Preparation of naphthalene-2-carboxylic acid[6-(2-methyl-pyridine-3-yloxy)-pyridine-3-yl]-amide EXAMPLE 8 Preparation of naphthalene-2-carboxylic acid[6-(2-methyl-pyridine-3-yloxy)-pyridine-3-yl]-amide The bispyridine ester amine compound (90 mg, 0.46 mmol) in Example 1 and 2-naphthoic acid (80 mg, 0.46 mmol) were dissolved in DMF (5 ml), DCC (90 mg, 0.46 mmol) was added to the solution, and the mixture was stirred at 60° C. for 8 hours. After the reaction was completed, the product was washed and filtered to yield a target compound as a brown solid (16 mg, 10%) by chromatography (methanol:dichloromethane=1:30).
10%	With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 60℃; for 8h;	8 The bispyridine ester amine compound (90 mg, 0.46 mmol) in Example 1 and 2-naphthoic acid (80 mg, 0.46 mmol) were dissolved in DMF (5 mℓ#8467;), DCC (90 mg, 0.46 mmol) was added to the solution, and the mixture was stirred at 60 °C for 8 hours. After the reaction was completed, the product was washed and filtered to yield a target compound as a brown solid (16 mg, 10 %) by chromatography (methanol: dichloromethane = 1:30).
10%	With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 60℃; for 8h;	8 Preparation of naphthalene-2-carboxylic acid[6-(2-methyl-pyridine-3-yloxy)-pyridine-3-yl]-amide The bispyridine ester amine compound (90 , 0.46 mmol) in Example 1 and 2-naphthoic acid (80 , 0.46 mmol) were dissolved in DMF (5 ), DCC (90 , 0.46 mmol) was added to the solution, and the mixture was stirred at 60 for 8 hours. After the reaction was completed, the product was washed and filtered to yield a target compound as a brown solid (16 , 10 %) by chromatography (methanol : dichloromethane = 1:30).

Reference： [1]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - US2009/258876, 2009, A1 Location in patent: Page/Page column 9
[2]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - EP2108649, 2009, A1 Location in patent: Page/Page column 14; 24
[3]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - WO2009/125923, 2009, A2 Location in patent: Page/Page column 26

46
[ 93-09-4 ]
[ 92-70-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	With oxygen; potassium acetate; palladium diacetate; p-benzoquinone In N,N-dimethyl acetamide at 115℃; for 15h;
53%	With tert.-butylhydroperoxide; (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; potassium acetate; palladium diacetate; p-benzoquinone In 1,2-dimethoxyethane; water at 100℃;
	With oxygen; potassium acetate; palladium diacetate; p-benzoquinone In N,N-dimethyl acetamide at 115℃; for 15h; Schlenk technique; regioselective reaction;	(21) Synthesis of para-Hydroxylated Arenes General procedure: A 50 mL Schlenk-type tube (with a Teflon high-pressure valveand side arm) was charged with m-toluic acid (68.0 mg, 0.50mmol), benzoquinone (54.0 mg, 0.50 mmol), KOAc (98.0 mg,1.00 mmol), Pd(OAc)2 (11.2 mg, 0.050 mmol), and N,N-dimethylacetamide(1.5 mL). The reaction tube was evacuated and backfilledwith O2 (3×, ballon). After the reaction mixture wasstirred at 115 °C for 15 h, it was allowed to cool down to r.t. Thereaction mixture was diluted with EtOAc (10 mL) and then filteredthrough a pad of Celite. The filtrate was concentrated invacuo to yield crude 2-hydroxylbenzoic acid. A mixture of thecrude product, Cu2O (3.6 mg, 0.025 mmol), and 1,10-phenanthroline(9.0 mg, 0.050 mmol) in a solution of NMP (1.5 mL) andquinoline (0.5 mL) was heated under an atmosphere of N2 at220 °C for 12 h. The reaction mixture was quenched by additionof 0.2 M aq HCl (10 mL), diluted with EtOAc (10 mL), and thenfiltered through a pad of Celite. The filtrate was washed withbrine (10 mL), dried over Na2SO4, and concentrated in vacuo.The residue was purified by silica gel preparative TLC to give pcresol.

Reference： [1]Zhang, Yang-Hui; Yu, Jin-Quan [Journal of the American Chemical Society, 2009, vol. 131, # 41, p. 14654 - 14655]
[2]Luo, Feihua; He, Shuhua; Gou, Quan; Chen, Jinyang; Zhang, mingzhong [Tetrahedron Letters, 2021, vol. 84]
[3]Pan, Shulei; Zhou, Bo; Zhang, Yanghui; Shao, Changdong; Shi, Guangfa [Synlett, 2016, vol. 27, # 2, p. 277 - 281]

47
[ 4316-98-7 ]
[ 93-09-4 ]
[ 1170069-83-6 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 3389 - 3393

48
[ 127896-08-6 ]
[ 35661-40-6 ]
[ 93-09-4 ]
[ 1256164-17-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Fmoc-N-propargylamine With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; copper(l) iodide; sodium L-ascorbate In water for 24h; solid phase reaction; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.333333h; solid phase reaction; Stage #3: N-Fmoc L-Phe; naphthalene-2-carboxylate Further stages;

Reference： [1]Cohrt, A. Emil; Jensen, Jakob F.; Nielsen, Thomas E. [Organic Letters, 2010, vol. 12, # 23, p. 5414 - 5417]

49
[ 6232-11-7 ]
[ 93-09-4 ]
[ 471924-96-6 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: naphthalene-2-carboxylate With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane for 0.5h; Cooling with ice; Stage #2: methyl 4-(aminomethyl)benzoate hydrochloride In dichloromethane at 20℃;	1.a Synthesis of compound 1 [methyl 4-((2-naphthylamide)methyl)benzoate] At room temperature, 2-naphthoic acid (345mg, 2mmol) was placed in a 100mL eggplant-shaped bottle,Add 30 mL of dichloromethane to dissolve. Add 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC*HCl) (460mg, 2.4mmol), 1-hydroxybenzotriazole (HOBt) under ice bath (325 mg, 2.4 mmol) and triethylamine (506 mg, 5 mmol), reacted for 0.5 hours. Methyl 4-aminomethylbenzoate hydrochloride (483 mg, 2.4 mmol) was added and reacted at room temperature overnight. TLC detected that the reaction of the raw materials was complete, then the reactant was washed with water (20 mL×3), and the organic phase was dried with anhydrous Na 2 SO 4 . After separation by column chromatography, compound 1 (415 mg, yield 65%) was obtained as a white solid, which was directly used in the next synthesis.
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;

Reference： [1]Current Patent Assignee: OCEAN UNIVERSITY OF CHINA - CN113831338, 2021, A Location in patent: Paragraph 0120; 0123-0124
[2]Location in patent: experimental part Kim, In-Hae; Park, Yong-Kyu; Hammock, Bruce D.; Nishi, Kosuke [Journal of Medicinal Chemistry, 2011, vol. 54, # 6, p. 1752 - 1761]

50
[ 93-09-4 ]
[ 116632-14-5 ]

Reference： [1]Patent: WO2011/44394,2011,A1

51
[ 93-09-4 ]
[ 224040-86-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3726 - 3729

52
[ 93-09-4 ]
[ 113443-62-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3726 - 3729
[2]Journal of the American Chemical Society,2014,vol. 136,p. 15248 - 15256

53
[ 76272-36-1 ]
[ 93-09-4 ]
[ 1335036-76-4 ]

Yield	Reaction Conditions	Operation in experiment
36.6%		General procedure: A solution of aromatic acid (5 mmol), ethyl chloroformate (0.5 mL, 5 mmol) and triethylamine (0.75 mL, 5 mmol) in anhydrous DMF (30 mL) was stirred for 30 min at 0 C. Subsequently, a solution of amine 3a, 3b or 3c (5 mmol) in anhydrous DMF (5 mL) was added dropwise. The cooling bath was removed and stirring was continued for 24 h. The solvent was evaporated in vacuo and the residue was dissolved in CH2Cl2 (30 mL). The solution was washed with a 5% aqueous solution of Na2CO3, dried with magnesium sulphate, filtered, and the solvent was evaporated in vacuo. The residue was recrystallised (for solid compounds), purified by column chromatography or treated with the appropriate acid to form crystalline salts (for oily compounds), as described below.

Reference： [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 4474 - 4488

54
[ 93-09-4 ]
[ 116632-14-5 ]
[ 90016-93-6 ]

Reference： [1]Synthetic Communications,2012,vol. 42,p. 635 - 638

55
[ 494769-44-7 ]
[ 93-09-4 ]
[ 1363397-41-4 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 8h;	General procedure: The intermediate (3) (0.5 g, 0.00217 mol), EDCl (0.622 g, 0.00325 mol), DMAP (0.345 g, 0.0028 mol) were stirred in dichloromethane (6 mL) at 0 C, and the substituted acid (0.00217 mol) were dissolved in (4 mL) of dichloromethane and charged to the reaction mixture and stirred at room temperature for 8 h. The reaction completion was monitored by TLC. Reaction was completed. The reaction mixture was diluted with (10 mL) of dichloromethane, and was washed with 10% NaHCO3 (10 mL). Separated the organic layer and was washed with saturated brine solution (10 mL). The organic layer was dried over sodium sulfate and concentrated the organic layer under reduced pressure to afford compounds 4a-t. The spectral data of compounds 4(a-t) are given below.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 49,p. 172 - 182

56
[ 19213-72-0 ]
[ 93-09-4 ]
[ 3007-91-8 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 1970 - 1973

57
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-18-9 ]
[ 71989-26-9 ]
[ 132327-80-1 ]
[ 109425-51-6 ]
[ 143824-78-6 ]
[ 93-09-4 ]
[ 159611-02-6 ]
[ 1376605-23-0 ]

Yield	Reaction Conditions	Operation in experiment
		First of all, N-terminal furan-StrepTagII peptides in solution were synthesized. Synthesis of a StrepTagII with N-terminal (2-furyl)-alanine was performed with solid-phase peptide synthesis on a 2-chlorotrityl chloride resin as shown in FIG. 8. The first amino acid, Fmoc-lysine, was manually coupled. After deprotection of Fmoc with piperidine in DMF, the synthesis of the StrepTagII continued automatically. <strong>[159611-02-6]Fmoc-(2-furyl)-alanine</strong> was subsequently coupled to the StrepTagII followed by Fmoc deprotection with piperidine in DMF and capping with 2-naphtoic acid. Subsequently, the N-terminal furan-StrepTagII was cleaved with a cleavage cocktail comprising TFA, TIS and water (95:2.5:2.5). Cleavage products were obtained comprising substantially pure N-terminal furan-StrepTagII peptides 5.2 capped with 2-naphtoic acid. Indeed, a composition was obtained comprising substantially pure N-terminal furan-peptides in solution. The degradation of the furan moiety during acidic cleavage was avoided by using a capping moiety

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 3999 - 4002
[2]Patent: US9290537,2016,B2 .Location in patent: Sheet 6/18

58
[ 124-38-9 ]
[ 91-58-7 ]
[ 93-09-4 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 9106 - 9109
[2]Organometallics,2020,vol. 39,p. 1476 - 1479
[3]Journal of the American Chemical Society,2017,vol. 139,p. 9467 - 9470

59
[ 93-09-4 ]
[ 613-56-9 ]

Reference： [1]Structural Chemistry,2012,vol. 23,p. 771 - 790,20

60
[ 101187-40-0 ]
[ 93-09-4 ]
[ 1407510-95-5 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 18388 - 18400

61
[ 101187-40-0 ]
[ 93-09-4 ]
[ 1407510-61-5 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 18388 - 18400

62
[ 1414927-98-2 ]
[ 86123-10-6 ]
[ 93-09-4 ]
[ 1414928-14-5 ]

Yield	Reaction Conditions	Operation in experiment
6.5 mg		General procedure: The chlorosilyl resin was swollen in dry DCM (20 mL) under argon atmosphere. A solution of imidazole (1.16 g, 17.0 mmol) and diol 5 (10.7 g, 16.8 mmol) in DCM (20 mL) was subsequently added. The mixture was vortexed overnight at room temperature using a Burrell wrist-action shaker. The loaded resin was washed with DCM (3 × 75 mL) and dried overnight under vacuum to provide 7.3 g of resin 6 (loading of 0.40 mmol/g). IR (KBr): nu 3442 (OH, alcohol), 1702 (C=O, carbamate) cm-1. The free diol 5 (8.7 g) was easily recovered after flash chromatography using EtOAc/hexanes (1:1) as eluent. A solution of piperidine in DCM (20% v/v) (70 mL) was added to resin 6 (7.3 g, 0.4 mmol/g) and the suspension was vortexed using a Burrell wrist-action shaker for 1 h at room temperature. The resin was then filtered and washed successively with DCM (5 × 75 mL) and MeOH (5 × 75 mL), and finally dried overnight to provide 6.5 g of Fmoc deprotected resin. The resin was divided into portions (1.80 g, 0.4 mmol/g in a 50 mL peptide flask). To each portion was added a solution of the appropriate amino acid (Fmoc-l-proline-OH (2.5 g, 7.5 mmol), Fmoc-d-proline-OH (2.5 g, 7.5 mmol), Fmoc-l-phenylalanine-OH (2.9 g, 7.5 mmol), Fmoc-d-phenylalanine-OH (2.9 g, 7.5 mmol) or Fmoc-l-tetrahydro-isoquinoline-3-carboxylic acid (3.0 g, 7.5 mmol), benzotriazole-yl-oxy-tris-pyrrolidinophosphonium hexafluorophosphate (PyBOP) (3.9 g, 7.5 mmol) and N-hydroxybenzotriazole (HOBt) (1.0 g, 7.5 mmol) in DMF (25 mL) under argon atmosphere. Diisopropylethylamine (DIPEA) (2.6 mL, 15 mmol) was added to the suspensions and the peptide flasks were vortexed with a Burrell wrist-action shaker for 5 h at room temperature. The resins were then filtered and washed successively with DCM (5 × 25 mL) and MeOH (5 × 25 mL), and finally dried overnight to give the resins 7. The coupling reaction was repeated a second time in each case in order to ensure complete coupling. A solution of piperidine in DCM (20% v/v) (70 mL) was added to resin 6 (7.3 g, 0.4 mmol/g) and the suspension was vortexed using a Burrell wrist-action shaker for 1 h at room temperature. The resin was then filtered and washed successively with DCM (5 × 75 mL) and MeOH (5 × 75 mL), and finally dried overnight to provide 6.5 g of Fmoc deprotected resin. The resin was divided into portions (1.80 g, 0.4 mmol/g in a 50 mL peptide flask). To each portion was added a solution of the appropriate amino acid (Fmoc-l-proline-OH (2.5 g, 7.5 mmol), Fmoc-d-proline-OH (2.5 g, 7.5 mmol), Fmoc-l-phenylalanine-OH (2.9 g, 7.5 mmol), Fmoc-d-phenylalanine-OH (2.9 g, 7.5 mmol) or Fmoc-l-tetrahydro-isoquinoline-3-carboxylic acid (3.0 g, 7.5 mmol), benzotriazole-yl-oxy-tris-pyrrolidinophosphonium hexafluorophosphate (PyBOP) (3.9 g, 7.5 mmol) and N-hydroxybenzotriazole (HOBt) (1.0 g, 7.5 mmol) in DMF (25 mL) under argon atmosphere. Diisopropylethylamine (DIPEA) (2.6 mL, 15 mmol) was added to the suspensions and the peptide flasks were vortexed with a Burrell wrist-action shaker for 5 h at room temperature. The resins were then filtered and washed successively with DCM (5 × 25 mL) and MeOH (5 × 25 mL), and finally dried overnight to give the resins 7. The coupling reaction was repeated a second time in each case in order to ensure complete coupling. To each of the resin-bound derivatives 8 was added 2 mL of an acid solution of 2 M methanolic HCl (AcCl + MeOH) in DCM (20:80, v/v) and the resulting suspensions were vortexed at 600 rpm for 1 h. DCM (1 mL) was added and the suspensions were filtered and the recovered filtrate was neutralized with 0.5 mL of 10% aqueous NaHCO3 (pH 8). The biphasic solution was filtered using a phase separator syringe (Biotage) and the resulting organic solution evaporated under reduced pressure. The 12 (3 × 4) crude amide compounds of library A (Table 2 ) were purified by filtration over a silica gel plug (10 mL) using EtOAc/hexanes (1:1) (15 mL) and then EtOAc (20 mL). In another experiment, the 28 (4 × 7) amide compounds of library B (Table 3 ) were evaporated to dryness and judged sufficiently pure by TLC and 1H NMR analyses for direct screening on HL-60 cells. All members of libraries A and B were analyzed by TLC, 1H NMR and LRMS.

Reference： [1]Steroids,2012,vol. 77,p. 1403 - 1418

63
[ 78162-58-0 ]
[ 93-09-4 ]
[ 13577-85-0 ]

Reference： [1]Journal of the Iranian Chemical Society,2012,vol. 9,p. 951 - 955

64
[ 464-49-3 ]
[ 93-09-4 ]
3-(2-naphthoyl)-(+)-camphor [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one With sodium hydride In 1,2-dimethoxyethane for 1h; Inert atmosphere; Reflux; Stage #2: naphthalene-2-carboxylate In 1,2-dimethoxyethane Inert atmosphere; Reflux;	2.1 4.2.1 3-(2-Naphthoyl)-(+)-camphor 5 (H2np) The β-diketone ligand 5 was prepared by a Claisen condensation.28 A dry 250 mL three-neck, round-bottomed flask fitted with a reflux condenser, pressure-equalizing addition funnel, and magnetic stirrer was maintained under a nitrogen atmosphere. Anhydrous 1,2-dimethoxyethane (50 mL), sodium hydride (2 g, 77.1 mmol), and (1R)-(+)-camphor (5.0 g, 32.8 mmol) were added to the flask and the mixture was stirred and refluxed for 1 h. Refluxing was continued as a solution of 2-naphthoate (6.13 g, 32.9 mmol) in 20 mL of anhydrous 1,2-dimethoxyethane was added dropwise over 90 min, after which the reaction was refluxed overnight. The flask was packed in ice and 10 mL of ethanol followed by 100 mL of distilled water were slowly added. The solution was brought to a pH of 1 with concentrated HCl. The solution was washed three times with 100 mL of pentane in a separatory funnel. The pentane layers were collected, washed four times with 100 mL of 5% sodium bicarbonate, and dried over sodium sulfate. The pentane was removed by rotary evaporation and the off-white solid was purified by recrystallization from pentane (7.7 g, 77%). 1H NMR (400 MHz, CDCl3) δ = 8.17 (s, 1H), 7.93-7.83 (m, 3H), 7.72 (dd, J = 8.6, 1.9 Hz 1H), 7.57-7.49 (m, 2H), 2.92 (d, J = 4.7 Hz 1H), 2.26-2.16 (m, 1H), 1.81 (m, 1H), 1.70 (m, 1H), 1.62-1.49 (m, 2H), 1.03 (s, 3H), 0.95 (s, 3H), 0.83 (s, 3H). And calcd for C21H22O2: C 82.35, H 7.19; Found C 82.17, H 7.39 (c 1.0, CHCl3).

Reference： [1]Clark, Rebecca L.; Wenzel, Bradford T.; Wenzel, Thomas J. [Tetrahedron Asymmetry, 2013, vol. 24, # 5-6, p. 297 - 304]

65
[ 2010-06-2 ]
[ 93-09-4 ]
[ 475044-85-0 ]

Yield	Reaction Conditions	Operation in experiment
64%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	General procedure for the synthesis of acetamide derivatives 4i-4l and 5i-5l General procedure: The key intermediates 3a or 3b (1 mmol), corresponding acids (1 mmol) and carbodiimide hydrochloride (EDC*HCl,1.5 mmol) and N-hydroxybenzotriazole (HOBt, 0.05 mmol) were stirred in CH2Cl2 (20-30 mL) at room temperature for 24 h. After that, the solvent was evaporated under reduced pressure to afford a residue, which was extracted with EtOAc (3 x 20 mL). The combined organic phases were dried with anhydrous Na2SO4. Removal of all the solvent under reduced pressure distillation to get the residue, which was purified with recrystallization to give target products 4i-4l and 5i-5l.
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	General procedure for the synthesis of 2-phenyl-N-(4-phenylthiazol-2-yl) acetamide derivatives 3a-3l and 4a-4l General procedure: For the synthesis of compounds 3a-3h, 3j, 3k, 4a-4h, 4j, 4k, a mixtureof corresponding acids (1 mmol), 4-phenylthiazol-2-ylamine derivatives (2a or 2b, 1 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl, 1.5 mmol), 1-hydroxybenzotrizole (HOBt, 0.05 mmol) in CH2Cl2 (20-30mL) was stirred at room temperature for 24 h. After that, the solvent was removed in vacuo to afford a residue, which was extracted with EtOAc (3 ×20mL). The combined organic phases were dried with anhydrous Na2SO4. Removal of all the solvent in vacuo resulted in a residue, which was purified with recrystallization to give target products.

Reference： [1]Li, Jing-Ran; Li, Dong-Dong; Wang, Rong-Rong; Sun, Jian; Dong, Jing-Jun; Du, Qian-Ru; Fang, Fei; Zhang, Wei-Ming; Zhu, Hai-Liang [European Journal of Medicinal Chemistry, 2014, vol. 75, p. 438 - 447]
[2]Cheng, Kui; Xue, Jia-Yu; Zhu, Hai-Liang [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 14, p. 4235 - 4238]

66
[ 2103-94-8 ]
[ 93-09-4 ]
[ 461410-43-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	General procedure for the synthesis of acetamide derivatives 4i-4l and 5i-5l General procedure: The key intermediates 3a or 3b (1 mmol), corresponding acids (1 mmol) and carbodiimide hydrochloride (EDC*HCl,1.5 mmol) and N-hydroxybenzotriazole (HOBt, 0.05 mmol) were stirred in CH2Cl2 (20-30 mL) at room temperature for 24 h. After that, the solvent was evaporated under reduced pressure to afford a residue, which was extracted with EtOAc (3 x 20 mL). The combined organic phases were dried with anhydrous Na2SO4. Removal of all the solvent under reduced pressure distillation to get the residue, which was purified with recrystallization to give target products 4i-4l and 5i-5l.
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	General procedure for the synthesis of 2-phenyl-N-(4-phenylthiazol-2-yl) acetamide derivatives 3a-3l and 4a-4l General procedure: For the synthesis of compounds 3a-3h, 3j, 3k, 4a-4h, 4j, 4k, a mixtureof corresponding acids (1 mmol), 4-phenylthiazol-2-ylamine derivatives (2a or 2b, 1 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl, 1.5 mmol), 1-hydroxybenzotrizole (HOBt, 0.05 mmol) in CH2Cl2 (20-30mL) was stirred at room temperature for 24 h. After that, the solvent was removed in vacuo to afford a residue, which was extracted with EtOAc (3 ×20mL). The combined organic phases were dried with anhydrous Na2SO4. Removal of all the solvent in vacuo resulted in a residue, which was purified with recrystallization to give target products.

67
[ 56503-39-0 ]
[ 93-09-4 ]
C₁₆H₁₂N₂O₄ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 5420 - 5431

68
[ 583-61-9 ]
cobalt pivalate [ No CAS ]
[ 75-05-8 ]
[ 93-09-4 ]
[Co₃(β-naphthoate)₆(2,3-lutidine)₂]*3(acetonitrile) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	In tetrahydrofuran; at 50℃; for 1h;	2,3-Lut (0.04 mL, 0.39 mmol) and a solution of beta-naphthoic acid (0.26 g, 1.535 mmol) in acetonitrile (30 mL) were added to a solution of [Co(Piv)2]n (0.1 g, 0.39 mmol) in THF (30 mL). The reaction mixture was vigorously stirred at 50C for 1 h until the initial reactants were dissolved completely. The obtained solution was cooled to room temperature and kept for 2 days. Precipitated violet crystals suitable for X-ray diffraction analysis were decanted from the mother liquor, washed with cold THF, and dried in air. The yield of compound III was 0.14 g (68% based on Co(Piv)2).

Reference： [1]Russian Journal of Coordination Chemistry,2015,vol. 41,p. 182 - 188
Koord. Khim.,2015,vol. 41,p. 182 - 188,7

69
[ 583-61-9 ]
[Cu^II₂(O₂C^tBu)₄(HO₂C^tBu)₂] [ No CAS ]
[ 93-09-4 ]
[Cu₂(β-naphthoate)₄(2,3-lutidine)₂] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In acetonitrile; at 75℃; for 0.5h;	An excess of 2,3-Lut (1 mL) was added to a solution of [Cu2(Piv)4(Piv)2] (0.1 g, 0.136 mmol) in MeCN (30 mL). The obtained reaction mixture was stirred at 75C for 30 min, then beta-naphthoic acid (0.140 g,0.816 mmol) was added, and the mixture was stirred for 30 min more. Precipitated blue crystals suitable for X-ray diffraction analysis were decanted from the mother liquor, washed with cold MeCN, and dried in air. The yield of compound II was 0.12 g (84% based on the initial amount of [Cu2(Piv)4(Piv)2]).

Reference： [1]Russian Journal of Coordination Chemistry,2015,vol. 41,p. 182 - 188
Koord. Khim.,2015,vol. 41,p. 182 - 188,7

70
[ 89-73-6 ]
calcium perchlorate tetrahydrate [ No CAS ]
manganese(II) perchlorate hexahydrate [ No CAS ]
[ 121-44-8 ]
[ 93-09-4 ]
(NHEt₃)₂[Mn₄Ca(2-naphthoato)₄(salicylhydroxime-H₃)₄] [ No CAS ]

Reference： [1]Inorganic Chemistry,2015,vol. 54,p. 2137 - 2151

71
[ 137-09-7 ]
[ 93-09-4 ]
[ 95888-12-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With polyphosphoric acid (PPA); at 180℃;	Synthesis Example 2 Synthesis of 2-(naphthalene-2-yl)benzo[d]oxazole-5-amine (Derivative No.3) 2-(naphthalene-2-yl)benzo[d]oxazole-5-amine (Derivative No.3) was synthesized according to Reaction Scheme 2 below: 80 mumol of 2,4-diaminophenol.2HCl and 80 mumol of naphthalene-2-carboxylic acid were dissolved in 100 mg of PPA, and then, the mixed solution was stirred at a temperature of 180 C. for 3 to 4 hours. After completion of the reaction, the reaction solution was cooled, neutralized with 10% NaOH, and filtered by using distilled water for recrystallization in a slow manner, thereby obtaining 15.6 mg of 2-(naphthalene-2-yl)benzo[d]oxazole-5-amine (Derivative No.3) (yield: 75%). 1H NMR (400 MHz, Chloroform-d) delta 8.53 (d, J=1.5 Hz, 1H), 8.17 (dt, J=7.5, 1.8 Hz, 1H), 8.09 (dd, J=7.5, 1.4 Hz, 1H), 8.01-7.92 (m, 2H), 7.52 (dtd, J=21.4, 7.4, 1.7 Hz, 2H), 7.29 (d, J=1.6 Hz, 1H), 7.21 (d, J=7.6 Hz, 1H), 6.84 (dd, J=7.5, 1.5 Hz, 1H), 3.38 (s, 2H).
75%	With polyphosphoric acid (PPA); at 180℃;	Synthesis Example 2 Synthesis of 2-(naphthalene-2-yl)benzo[d]oxazole-5-amine (Derivative 3) (0079) 2-(naphthalene-2-yl)benzo[d]oxazole-5-amine (Derivative 3) was synthesized according to Reaction Scheme 2 below: (0080) (0081) 80 mumol of 2,4-diaminophenol.2HCl and 80 mumol of naphthalene-2-carboxylic acid were dissolved in 100 mg of PPA, and then, the mixed solution was stirred at a temperature of 180 C. for 3 to 4 hours. After completion of the reaction, the reaction solution was cooled, neutralized with 10% NaOH, and filtered by using distilled water for recrystallization in a slow manner, thereby obtaining 15.6 mg of 2-(naphthalene-2-yl)benzo[d]oxazole-5-amine (Derivative 3) (yield: 75%). (0082) 1H NMR (400 MHz, Chloroform-d) delta 8.53 (d, J=1.5 Hz, 1H), 8.17 (dt, J=7.5, 1.8 Hz, 1H), 8.09 (dd, J=7.5, 1.4 Hz, 1H), 8.01-7.92 (m, 2H), 7.52 (dtd, J=21.4, 7.4, 1.7 Hz, 2H), 7.29 (d, J=1.6 Hz, 1H), 7.21 (d, J=7.6 Hz, 1H), 6.84 (dd, J=7.5, 1.5 Hz, 1H), 3.38 (s, 2H).

Reference： [1]Patent: US2015/197498,2015,A1 .Location in patent: Paragraph 0073; 0074; 0075
[2]Patent: US9447054,2016,B2 .Location in patent: Page/Page column 11

72
[ 2243-82-5 ]
[ 93-09-4 ]

Yield	Reaction Conditions	Operation in experiment
	With cell-free extract of amidase gene cloned from Klebsiella oxytoca KCTC 1686 and functionally expressed in Escherichia coli BL21(DE3); In methanol;Enzymatic reaction;	General procedure: The substrate specificity of recombinant KamH was tested using various aliphatic and aromatic amides. Cell-free extract of E. coli BL21(DE3)/pET-Ami2 was mixed with various concentrations of substrate under standard reaction conditions; 10percent (v/v) methanol was added as cosolvent to solubilize the substrate. The enzyme activity toward the various amides was determined by monitoring the formation of either carboxylic acid or ammonia [36]. Several racemic amides were used to study the stereoselectivity of the recombinant enzyme, including 2-phenylacetamide, mandelamide, 2,2-dimethylcyclopropanecarboxamide, and 2-(4-chlorophenyl)-3-methylbutyramide. Enantiomeric excess values were obtained by HPLC analysis using an AY-RH column. The enantiomeric excess and enantiomeric ratio of the product were determined according to Chen et al. [37].

Reference： [1]Process Biochemistry,2015,vol. 50,p. 1264 - 1271

73
[ 124-38-9 ]
[ 532-02-5 ]
[ 93-09-4 ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2022 - 2026

74
[ 1539-42-0 ]
[ 93-09-4 ]
N,N-bis(pyridin-2-ylmethyl)naphthalene-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: naphthalene-2-carboxylate With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In dichloromethane at 20℃; for 0.0833333h; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Stage #3: bis[(2-pyridyl)methyl]amine In dichloromethane at 20℃; for 16h;	3.3 N,N-Bis(pyridin-2-ylmethyl)naphthalene-2-carboxamide (NaphBPA 1) 2-Naphthoic acid (482mg, 2.8mmol, 1.4equiv.) and TBTU (899mg, 2.8mmol, 1.4equiv.) were suspended in DCM (25ml). After stirring for 5minat rt, DIPEA (2.1ml, 12mmol, 6.0equiv.) was added and the reaction mixture was allowed to become a clear solution. Finally, N,N-bis(2-picolylamine) (400mg, 2.0mmol, 1.0equiv.) was added and the reaction mixture was stirred for further 16h at rt. The reaction mixture was then washed with water (2×15ml) and the organic phase was dried with Na2SO4. The solvent was removed under reduced pressure and the residue was purified via column chromatography (silica gel, DCM→DCM/MeOH 95:5). A pale yellow gum which still contained a significant amount of tetramethyl urea was obtained after column chromatography. The tetramethyl urea was then removed by the addition of cold Et2O. The insoluble material was filtered and dried in vacuum (443mg, 1.25mmol, 63%). N,N-bis(pyridin-2-ylmethyl)naphthalene-2-carboxamide (dubbed as NaphBPA): m.p.: 102-103°C, 1H NMR (CDCl3, 400MHz): δ=4.75 (s, 2H, PyCH2-), 4.94 (s, 2H, PyCH2-), 7.18-7.21 (m, 3H, Harom.), 7.46-7.52 (m, 3H, Harom.), 7.62-7.84 (m, 6H, Harom.), 8.07 (mc, 1H, Harom.), 8.57 (br. s, 2H, Harom.) ppm, 13C NMR (CDCl3, 100MHz): δ=50.6, 54.6, 121.5, 122.4, 122.7, 124.4, 126.6, 126.9, 127.0, 127.8, 128.3, 128.5, 132.7, 133.3, 133.8, 136.7, 149.3, 149.9, 156.7, 157.2, 172.6ppm, MS (pos. APCI): m/z (%)=354.2 (100) [(M+H)+], HRMS (pos. APCI, MeOH) m/z [(M+H)+]: Calcd. for C23H20N3O: 354.16064, found: 354.16070, Anal. for C23H19N3O: Calcd.: C, 78.16, H, 5.42, N, 11.89, found: C, 77.77, H, 5.38, N, 11.93., selected IR: =1649, 1630, 1591, 1572, 1477, 1454, 1439, 1406cm-1.

Reference： [1]Jakob, Uwe; Petersen, Thies Olaf; Bannwarth, Willi [Journal of Organometallic Chemistry, 2015, vol. 797, p. 46 - 51]

75
[ 41873-65-8 ]
[ 93-09-4 ]
ethyl 2-(2-naphthoyloxy)phenylacetate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 8254 - 8261

76
[ 124-38-9 ]
[ 612-55-5 ]
[ 93-09-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 3,4-benzo-1,1,2,2-tetraethyl-1,2-disilacyclobut-3-ene; cesium fluoride In N,N-dimethyl-formamide at 0 - 20℃; for 2h;

Reference： [1]Mita, Tsuyoshi; Suga, Kenta; Sato, Kaori; Sato, Yoshihiro [Organic Letters, 2015, vol. 17, # 21, p. 5276 - 5279]

77
[ 121148-01-4 ]
[ 93-09-4 ]
C₂₁H₂₄N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of compound 3 (0.72 g, 2.0 mmol) and 4-Methylmorpholine (0.61 g, 6. 0 mmol) in dichloromethane (50 mL), HOBt (0.32 g, 2.4 mmol) and EDCI (0.49 g, 2.4 mmol) was added, and the mixture was stirred at room temperature for 0.5 h. After compound 4a was added, the solution was stirred overnight. The solvent was evaporated, and the obtained residue was extracted with ethyl acetate. The combined extracts were washed with saturated NaHCO3, 1 M aqueous HCl, brine, dried over anhydrous MgSO4, and concentrated to yield the crude product which was purified by column chromatography eluting with PE/EA (1:1 v/v) to give compound 5a as white solid (0.58 g, yield: 46.2%);

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 5539 - 5545

78
[ 71-43-2 ]
[ 93-09-4 ]
[ 3074-03-1 ]

Yield	Reaction Conditions	Operation in experiment
53%	With sodium persulfate; (2S,3S)-N-acetyl-2-amino-3-methylpentanoic acid; trifluorormethanesulfonic acid; palladium diacetate In dimethyl sulfoxide at 80℃; for 24h; Schlenk technique;

Reference： [1]Sun, Denan; Li, Bijin; Lan, Jingbo; Huang, Quan; You, Jingsong [Chemical Communications, 2016, vol. 52, # 18, p. 3635 - 3638]

79
[ 93-09-4 ]
[ 528-44-9 ]
[ 88-99-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hypochlorite; ruthenium(III) chloride trihydrate; sulfuric acid; tetrabutylammomium bromide; In water; 1,2-dichloro-ethane; at 23℃; for 0.5h;pH 9.0;Green chemistry;	General procedure: In a 250-mL three necked flask equipped with pH and temperature sensor were placed 40 mL of aq. NaOCI (10 % Assay) at room temperature. The pH at the aqueous phase was brought to pH 9 ± 0.1 by addition of 20 % (v/v) H2SO4. To this aqueous NaOCl solution; mixture of naphthalene (0.81 g, 5 mmol), RuCl3*3H2O (0.0065 g,0.5 mol%), tetrabutyl ammonium bromide (0.040 g, 2.5 mol%) and 10 mL of 1,2-dichloroethane were added. Stirring was commenced with a mechanical stirrer and reaction continued at room temperature (23 ± 2 C) duringthe period of 10-30 min. The pH was controlled during the reaction by using manual addition of 20 % of NaOH to keep the pH at 9 ± 0.1. After the hypochlorite solution was used up (reaction shows colour change from yellow to white cloudy) a few drops of hypochlorite solution were added to reoxidize the ruthenium catalyst. The phases were separated and an aqueous phase is acidified with dilute 20 % aq. H2SO4 to brought pH at 2.5-3. The acidic solution containing organic products was extracted with diethylether (30 x 3 = 90 mL); solvent evaporation resulted into crude 3-chlorophthalic acid (0.842 g, 4.2 mmol). Derivatization of phthalic acids using N, O-bis(trimethylsilyl)trifluoroacetamide with 1 % trimethylchlorosilane (BSTFA) was performed for gc analysis.

Reference： [1]Catalysis Letters,2016,vol. 146,p. 991 - 997

80
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-18-9 ]
[ 71989-26-9 ]
[ 132327-80-1 ]
[ 109425-51-6 ]
[ 143824-78-6 ]
[ 93-09-4 ]
[ 159611-02-6 ]
C₆₈H₈₀N₁₄O₁₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Secondly, in order to test the influence of the position of the furan amino acid in the furan-peptide on cross-linking, free furan-StrepTagII peptides were synthesized in which the furan amino acid was C-terminally incorporated. Synthesis of a StrepTagII with C-terminal (2-furyl)-alanine was performed on 2-chlorotrityl chloride resin as shown in FIG. 9. The first amino acid, <strong>[159611-02-6]Fmoc-(2-furyl)-alanine</strong>, was manually coupled. After deprotection of Fmoc with piperidine in DMF, the synthesis of the StrepTagII continued automatically. The C-terminal furan-StrepTagII was N-terminally capped with 2-naphtoic acid. Because 2-naphtoic acid has a specific absorbance in the UV-VIS spectrum, its incorporation in the StrepTagII could ease the identification of labeled streptavidin. Subsequently, the C-terminal furan-StrepTagII was cleaved with a cleavage cocktail comprising TFA, TIS and water (95:2.5:2.5). Cleavage products comprising substantially pure C-terminal furan-StrepTagII peptides 5.3 were obtained. Indeed, C-terminal modification of the peptide with a furan-moiety was obtained using <strong>[159611-02-6]Fmoc-(2-furyl)-alanine</strong>.

Reference： [1]Patent: US9290537,2016,B2 .Location in patent: Sheet 6/18

81
[ 77-78-1 ]
[ 93-09-4 ]
[ 2471-70-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide; In 1,4-dioxane; water; at 65℃; for 5h;	The reaction flask was added 3.5 g (24mmol) 2- naphthoic acid and 30 ml of 1,4-dioxane, stirred to dissolve, heating To 65 C, solution containing 4.85 g (120mml) aqueous sodium hydroxide solution, the reaction temperature 65 C, the slow add 3.5 g (28_1) of dimethyl sulfate (3 drops 5 minutes), 5 hours, suction filtered, evaporated under reduced pressure 1,4_ dioxane, precipitated solid Body, suction, washed with a light yellow solid 3.4 g, yield 90%

Reference： [1]Patent: CN101602750,2016,B .Location in patent: Paragraph 0081; 0082

82
[ 75-24-1 ]
[ 93-09-4 ]
[ 39110-32-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: trimethylaluminum; naphthalene-2-carboxylate With iron(III)-acetylacetonate; 4-(bis(2-(diphenylphosphanyl)phenyl)phosphanyl)-N,N-dimethylaniline In tetrahydrofuran; 1,2-dimethoxyethane; toluene at 20℃; Inert atmosphere; Schlenk technique; Stage #2: With 2,3-dichlorobutane In tetrahydrofuran; 1,2-dimethoxyethane; toluene at 70℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;

Reference： [1]Shang, Rui; Ilies, Laurean; Nakamura, Eiichi [Journal of the American Chemical Society, 2016, vol. 138, # 32, p. 10132 - 10135]

83
bis(trimethylaluminium)-1,4-diazabicyclo[2.2.2]octane adduct [ No CAS ]
[ 93-09-4 ]
[ 39110-32-2 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: bis(trimethylaluminium)-1,4-diazabicyclo[2.2.2]octane adduct; naphthalene-2-carboxylate With iron(III)-acetylacetonate; 4-(bis(2-(diphenylphosphanyl)phenyl)phosphanyl)-N,N-dimethylaniline In tetrahydrofuran; 1,2-dimethoxyethane; toluene at 20℃; Inert atmosphere; Schlenk technique; Stage #2: With 2,3-dichlorobutane In tetrahydrofuran; 1,2-dimethoxyethane; toluene at 70℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;

Reference： [1]Shang, Rui; Ilies, Laurean; Nakamura, Eiichi [Journal of the American Chemical Society, 2016, vol. 138, # 32, p. 10132 - 10135]

84
[ 568-72-9 ]
[ 93-09-4 ]
1,6,6-trimethyl-10,11-dioxo-6,7,8,9,10,11-hexahydrophenanthro[1,2-b]furan-9-yl 2-naphthoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In chlorobenzene at 120℃; for 24h; Sealed tube; regioselective reaction;

Reference： [1]Ding, Chunyong; Li, Jie; Jiao, Mingkun; Zhang, Ao [Journal of Natural Products, 2016, vol. 79, # 10, p. 2514 - 2520]

85
[ 893-33-4 ]
[ 93-09-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With oxygen; sodium hydrogencarbonate; In acetonitrile; for 4h;Molecular sieve; Irradiation;	General procedure: Photoredox catalyst [Ru(bpy)3]Cl2·6H2O (6.4mg, 0.01 mmol) was added to a stirred suspension of 2 mL CH3CN, beta-diketone 1n (222mg, 1.0 mmol), 4A molecular sieve (200 mg) and NaHCO3 (84 mg, 1.0 mmol), the mixture was stirred under irradiation of 20W blue LED and charged with oxygen balloon for 4h unless otherwise noticed, after completion of the reaction, the resulted suspension was acidified with 1% HCl before filtered through celite, the filtrate was concentrated before purified through silica gel chromatography (gradient elution with hexanes/ethyl acetate from 3/1 to 2/1) to yield the carboxylic acid 2n 9 ( 126mg, 0.99 mmol, 99%) as white solid. (M. p = 125-129 oC) 1H NMR (DMSO-d6, 400 MHz, ppm) delta 13.06 (s, br, 1H), 7.88 (d, 1H, J = 4.8 Hz), 7.74 (d, 1H, J = 3.8 Hz); 13C NMR (DMSO-d6, 100 MHz, ppm) delta 163.4, 135.2, 133.8, 133.7, 128.7.

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 5628 - 5631

86
[ 98998-25-5 ]
[ 93-09-4 ]
N-(8-methyl-8-azabicyclo[3.2.1]oct-3β-yl)-2-naphthamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40.7%	Stage #1: naphthalene-2-carboxylate With triethylamine In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: (Endo)-8-methyl-8-azabicyclo[3.2.1]-octan-3-amine In N,N-dimethyl-formamide for 24h; Cooling;	2 General remarks A solution of naphthalene-2-carboxylic acid (18.9 g, 0.11 mol), ethyl chloroformate (10.5 mL, 0.11 mol) and triethylamine (16.5 mL, 0.12 mol) in anhydrous DMF (200 mL) was stirred for 30 min at 0 °C. After this time a solution of amine 3 (16.5 g, 0.12 mol) in anhydrous DMF (40 mL) was added dropwise. The cooling bath was removed and stirring was continued for 24 h. The solvent was evaporated in vacuo and the residue was dissolved in CH2Cl2 (150 mL). The solution was washed with a 5% aqueous solution of Na2CO3 (3 * 50 mL), then with 5% NaOH (2 * 50 mL) and once with 100 mL of water. The organic layer was dried with magnesium sulphate, filtered, and concentrated in vacuo. The solid residue was purified by crystallisation from ethyl acetate. Yield:14.1 g (40.7%), mp 200.7-201.8 °C. IR (KBr) cm-1: ν 3247 (NH), 1632 (CO); ESI-HRMS m/z calcd for C19H22N2OH (M+H)+ 295.1810, found: 295.1812.

Reference： [1]Stefanowicz, Jacek; Słowiński, Tomasz; Wróbel, Martyna Zofia; Herold, Franciszek; Gomółka, Anna Edyta; Wesołowska, Anna; Jastrzębska-Więsek, Magdalena; Partyka, Anna; Andres-Mach, Marta; Czuczwar, Stanisław Jerzy; Łuszczki, Jarogniew Jacek; Zagaja, Mirosław; Siwek, Agata; Nowak, Gabriel; Żołnierek, Maria; Bączek, Tomasz; Ulenberg, Szymon; Belka, Mariusz; Turło, Jadwiga [Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 3994 - 4007]

87
[ 93-09-4 ]
[ 573-97-7 ]

Yield	Reaction Conditions	Operation in experiment
82%	With dihydrogen peroxide; acetic acid; potassium bromide at 20℃; for 10h;	1 4 mmol2-naphthoic acid and4 mmol potassium bromide was placed in a round bottom flask,5 ml of acetic acid was added,Stirring dropwise 4mmolHydrogen peroxide (30%), 20 ° C under stirring reaction 10h,After being cooled for 12h at 0 ° C, the product was filtered to obtain pale yellow needle-like crystals. After drying, the products were analyzed by IR and 1H-NMR.The yield was calculated by weighing, under the above conditionsThe yield of 1-bromo-2-naphthol was 82%.

Reference： [1]Current Patent Assignee: LIAOCHENG UNIVERSITY - CN104478667, 2016, B Location in patent: Paragraph 0027; 0028; 0029

88
[ 143-27-1 ]
[ 93-09-4 ]
N-hexadecylnaphthalene-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: naphthalene-2-carboxylate With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate In dichloromethane; acetonitrile at 20℃; for 0.166667h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile for 0.5h; Inert atmosphere; Stage #3: hexadecylamine In dichloromethane; acetonitrile at 20℃; Inert atmosphere;	4.1.8. N-Hexadecylnaphthalene-2-carboxamide (8) General procedure: All compounds were synthesized by a one-step coupling reaction. Briefly, in a general procedure the appropriate acid (1 eq), and (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholino-carbenium hexafluoro phosphate (COMU, 1 eq) were dissolved in anhydrous CH2Cl2/CH3CN (3/1) at room temperature under a nitrogen atmosphere. After 10 min diisopropylethylamine (2 eq) was added and the resulting orange-red solution was stirred for 30 min. Hexadecylamine (1 eq) in CH3CN was then injected into the reaction mixture and vigorous stirring at room temperature was continued until TLC confirmed the completion of the reaction (1-6 h). The reaction mixture was diluted with CH2Cl2 and washed with 5% HCl, saturated NaHCO3 and brine. The organic layers were collected, dried over anhydrous Na2SO4 and filtered. The solvent was evaporated under reduced pressure and crude purified by flash chromatography to give white solids and reaction yields range from 45% to 85%.
	With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 20℃; Reflux; Inert atmosphere;

Reference： [1]Vago, Riccardo; Bettiga, Arianna; Salonia, Andrea; Ciuffreda, Pierangela; Ottria, Roberta [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 3, p. 1242 - 1249]
[2]Casati, Silvana; Ciuffreda, Pierangela; Ottria, Roberta; Yancheva, Denitsa; Šmelcerović, Andrija; Lazarević, Jelena; Zvezdanović, Jelena [Chemico-Biological Interactions, 2020, vol. 326]

89
[ 105-83-9 ]
[ 93-09-4 ]
N,N'-[(methylazanediyl)bis(propane-3,1-diyl)]bis(2-naphthamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54.6%		General procedure: A mixture of acid 10-13 (10 mmol) and CDI (10 mmol) in acetonitrile (100 mL) or DMF (100 mL)was stirred for 1 h at room temperature. Then the appropriate polyamine (a-d) (6 mmol) was addedand stirring was continued for additional 2 h, then the mixture was filtered. The solvent was removedunder reduced pressure and 20 mL of H2O was added to the residue and left for 24 h at 5 C(for compounds 11a-d, 13a-d, 14a-d. Then the solid was filtered off, washed with H2O and crystallizedfrom DMF/H2O. In case of compounds 12a-d the residues were purified by column chromatographyover silica gel (CHCl3/MeOH, 100:1, 10:1, v/v).

Reference： [1]Molecules,2017,vol. 22

90
[ 93-09-4 ]
[ 256652-04-7 ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 7440 - 7443
[2]Organic Letters,2017,vol. 19,p. 4291 - 4294
[3]Synlett,2017,vol. 28,p. 2594 - 2598

91
[ 97-77-8 ]
[ 93-09-4 ]
[ 13577-84-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With di-tert-butyl peroxide; copper(I) bromide; In ethyl acetate; at 120℃;	General procedure: Benzoic acid (1.0 mml), tetramethylthiuram disulfide (TMTD) (1.1 mmol), CuBr (10% mmol), DTBP (di-tert-butyl peroxide, 2.0 equiv) were added in dried seal tube equipped with a septum and magnetic stirrer bar, EtOAc (ethyl acetate, 2 mL) was then added. The mixture was stirred at 120 oC and checked by TLC until the starting material was finished (about 10-12 h). The reaction was cooled down to room temperature, quenched with sat. NH4Cl solution (5 mL) and then extracted with ethyl acetate (10 mml). The crude solution was dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography to afford the desired product.

Reference： [1]Synthetic Communications,2017,vol. 47,p. 1434 - 1440

92
[ 5773-80-8 ]
[ 93-09-4 ]

Yield	Reaction Conditions	Operation in experiment
98.8%	With palladium 10% on activated carbon; potassium acetate; bis(pinacol)diborane; In ethanol; at 60℃; for 6h;Inert atmosphere;	General procedure: To a solution of brominated aromatic compounds (1 equiv),bis(pinacolate)diboron (1.5 equiv) and anhydrous ethanol (15 mL)were added10%palladium-carbon (0.01 equiv), followed by potassium acetate (3 equiv) under argon. The mixture was heated in a 60 C with stirring for the indicated time. Thereactor was cooled to room temperature, and the reaction mixture was filtered, and thefiltrate was concentrated under reduced pressure. The residue was extracted with dichloromethane (20 mL×3), and organic layer was washed with water (20 mL×2)and once with brine (25 mL), dried over magnesium sulfate and concentrated in vacuo.The product was purified by silica gel flash chromatography on silica gel usingpetroleum as eluent.

Reference： [1]Synlett,2018,vol. 29,p. 779 - 784

93
[ 93-09-4 ]
[ 612-55-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-iodo-succinimide; [4,4?-bis(1,1-dimethylethyl)-2,2?-bipyridine-N1,N1?]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; iodine; caesium carbonate; In 1,2-dichloro-ethane; at 50℃; for 24h;Inert atmosphere; Irradiation; Sealed tube;	General procedure: To a 15 mL test tube with septum Cs2CO3 (0.6 mmol, 195 mg), aromaticcarboxylic acid (1) (0.3 mmol), [Ir(dF(CF3)ppy)2dtbbpy]PF6 (D) (6 mummol, 6.7 mg), NIS (1.5mmol, 337.5 mg) and I2 (60 mumol, 20 mol%) were added. The tube was evacuated and backfilledwith argon for three times, and then 3 mL of dry DCE was added through a syringer under argon.The tube was sealed with Parafilm Mr and placed in an oil bath with a contact thermometer, andthe reaction was carried out at 50 C under irradiation with 6 × 5 W blue LEDs (lambdamax = 455 nm).After 24 h or 36 h, the resulting mixture was filtered through a 2 cm thick pad of silica, and thesilica was washed with DCM) (50 mL). The filtrate was collected and the solvent was removed invacuo. The crude residue was purified by silica gel flash column chromatography to provide thetarget product (2). (Note: The reaction was very sensitive to moisture, and the yields sharplydecreased to less than 5% when 0.01 equivalent of H2O was added to the reaction system).

Reference： [1]Synlett,2018,vol. 29,p. 1572 - 1577
[2]Angewandte Chemie - International Edition,2019,vol. 58,p. 10514 - 10520
Angew. Chem.,2019,vol. 131,p. 10624 - 10630,7

94
[ 67-56-1 ]
[ 2243-82-5 ]
[ 2459-25-8 ]
[ 93-09-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydrogensulfate; water; at 65℃; for 48h;	General procedure: A mixture of the amide (1, 1 mmol), alcohol (15 mL), and pulverized potassium bisulfate (1.1 g, 8 mmol) was refluxed for the specified time. The alcohol was removed in vacuo and the residue was triturated with hexanes (or other appropriate solvent such as DCM or ethyl acetate to dissolve the product). Removal of hexanes in vacuo provided the following pure products

Reference： [1]Arkivoc,2018,vol. 2018,p. 174 - 183

95
[ 73183-34-3 ]
[ 93-09-4 ]
[ 256652-04-7 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 16721 - 16726
Angew. Chem.,2018,vol. 130,p. 16963 - 16968,6

96
[ 29968-78-3 ]
[ 93-09-4 ]
C₁₉H₁₆N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl acetamide;	General procedure: To a solution of corresponding acids (RCOOH, 0.63 mmol), HOBt (170 mg, 1.26 mmol), EDCI (242 mg, 1.26 mmol), and DIPEA (0.208 mL, 1.26 mmol) were added to DMA (60 mL), and then 4 (186 mg, 1.26mmol) were added, the mixture was stirred overnight. The mixture was dissolved in water, then the aqueous solution was extracted with ethyl acetate (50 mL 3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by column chromatography to give N-(4-nitrophenethyl)amide (5) in a good yield. And to a solution of 5 in MeOH was added 10% Pd/C under H2 at reflux overnight, then the mixture was dissolved in water, then the aqueous solution was extracted with ethyl acetate (50 mL 3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by column chromatography to give N-(4-aminophenethyl)amide (6) in a good yield. Then the mixture of 3 and 6 was added NaCNBH3 in MeOH and the solution was stirred under reflux overnight. After reaction completed, the solvent was removed under reduced pressure and the residue was dissolved in water, the aqueous solution was extracted with ethyl acetate (50 mL 3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by column chromatography to afford the corresponding compounds (7-26) in good yields.

Reference： [1]Chinese Chemical Letters,2019,p. 250 - 254

97
[ 501-60-0 ]
[ 93-09-4 ]
(E)-5-methyl-2-(p-tolyldiazenyl)phenyl 2-naphthoate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 1038 - 1044

98
[ 93-09-4 ]
[ 3074-03-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: thionyl chloride; magnesium sulfate / 1,2-dichloro-benzene / 24 h / 120 °C / Inert atmosphere 2: silver(l) oxide; potassium carbonate; palladium diacetate; acetic acid / 24 h / 130 °C / Inert atmosphere 3: trifluorormethanesulfonic acid; acetic acid / 1 h / 130 °C

Reference： [1]Large, Benjamin; Gigant, Nicolas; Joseph, Delphine; Clavier, Gilles; Prim, Damien [European Journal of Organic Chemistry, 2019, vol. 2019, # 8, p. 1835 - 1841]

99
[ 55717-46-9 ]
[ 93-09-4 ]
N-(5-hydroxy-pyridin-2-yl)-2-naphthamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 16h;	7 Scheme II can be employed to form N-(4-hydroxyphenyl)amides. A mixture of 4-aminophenol (202, 1.0 mmol), DIPEA (2 mmol), HATU (1.5 mmol) and acid (201, 1.0 mmol) in N,N-dimethylformamide (5 mL) was stirred for 16 hours at ambient temperature. The mixture was concentrated and the residue was purified by Prep-HPLC with the following condition: Column: XBridge Prep OBD C18 Column 30xl50mm 5um;Mobile Phase A:Water (0.1%FA), Mobile Phase B: ACN; Flow rate: 60 mL/min; Gradient: 10% B to 45% B in 7 min; 254/220 nm, to afford amide 203.

Reference： [1]Current Patent Assignee: CENTAURUS THERAPEUTICS - WO2018/112077, 2018, A1 Location in patent: Paragraph 00246; 00259

100
[ 5388-42-1 ]
[ 93-09-4 ]
2-(1-oxoisoindolin-2-yl)phenyl 2-naphthoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; silver carbonate In 1,2-dichloro-ethane at 110℃; for 24h; Inert atmosphere; Schlenk technique;

Reference： [1]Yuan, Yu-Chao; Bruneau, Christian; Roisnel, Thierry; Gramage-Doria, Rafael [Organic and Biomolecular Chemistry, 2019, vol. 17, # 32, p. 7517 - 7525]

101
[ 26348-61-8 ]
[ 93-09-4 ]
C₁₆H₁₇NO₄ [ No CAS ]

Reference： [1]RSC Advances,2019,vol. 9,p. 26302 - 26314

102
[ 646-25-3 ]
[ 93-09-4 ]
N,N′-(decane-1,10-diyl)bis(2-naphthamide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 12h;	General procedure: Compounds 9e-35e were obtained by using one-pot reaction. A mixture of aromatic acid (6.30 mmol), EDCI (7.50 mmol), DMAP (0.60 mmol), and anhydrous dichloromethane (20 mL) was stirred to dissolve, then decane-diamine (3 mmol) was added and stirred at room temperature for 12 h. The mixture solution was filtered under reduced pressure. After that, the residue was washed with little amount of CH2Cl2and water successively, and dried to give the solid. Then, the residue was purified on preparative TLC eluted with chloroform/methanol = 40:1-7:1 to yield compounds 26e, 28e, 30e, and 31e.

Reference： [1]Molecules,2019,vol. 24

103
[ 33631-01-5 ]
[ 93-09-4 ]
N-(1-methyl-2-oxo-1,2-dihydropyridin-3-yl)-2-naphthamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2020,vol. 85,p. 345 - 359

104
[ 124-38-9 ]
[ 256652-04-7 ]
[ 93-09-4 ]

Reference： [1]ChemSusChem,2020,vol. 13,p. 2080 - 2088

105
[ 78871-05-3 ]
[ 93-09-4 ]
tri(naphthalen-2-yl)phosphine oxide [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2020,vol. 2020,p. 1148 - 1153

106
[ 2987-16-8 ]
3-fluoro-4-[(6,7-dimethoxyquinoline-4-yl)oxy]phenylisonitrile [ No CAS ]
[ 93-09-4 ]
1-((4-((6,7-dimethoxyquinolin-4-yl)oxy)-3-fluorophenyl)amino)-3,3-dimethyl-1-oxobutan-2-yl 2-naphthoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84.6%	In tetrahydrofuran; water at 40℃; for 24h;	4.1.4. General procedure for synthesis of 6,7-dimethoxy-4-(2-fluorophenoxy)quinoline derivatives bearing a-acyloxycarboxamidemoiety 10a-y General procedure: To a solution of aldehyde/ketone (0.4 mmol) in THF/H2O (0.5 mL,v/v 3:1) was added carboxylic acid (0.4 mmol) and 9 (0.2 mmol)at room temperature. The reaction mixture was subsequentlyheated at 40 C for 24 h. Upon completion of the reaction (TLCmonitoring), the mixture was cooled to room temperature andsolvent was evaporated. The residue was purified by chromatographyon silica gel using ethyl acetate/hexaneas eluent to give 10ay.

Reference： [1]Fang, Sen-Biao; Li, Hui-Jing; Li, Qin-Ying; Nan, Xiang; Wu, Yan-Chao [European Journal of Medicinal Chemistry, 2020, vol. 193]

107
[ 17557-67-4 ]
[ 93-09-4 ]
N-(6-methanesulfonyl-1,3-benzothiazol-2-yl) naphthalene-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%		A mixture of 2-naphthalenecarboxylic acid (CAS No. 93-09-4, 300 mg, 1.7 mmol), TBTU (75 mg, 0.87 mmol), and DIEA (322 mg, 2.5 mmol) in acetonitrile (10 mL) was stirred at RT for 15 min, followed by addition of 6-(methylsulfonyl)-2-benzothiazolamine (Intermediate amine 2) (435 mg, 1.9 mmol) in one portion at RT. The resulting mixture was stirred at RT for 12 h. The reaction mixture was diluted with DCM (12 mL) and filtered. The filter cake was purified through column chromatography (eluent: DCM:MeOH from 50:1 to 20:1) to afford the desired product (519 mg, 75%) as a white solid. LC/MS (ES+): found: 383.5 [M+H]. 1H NMR (400 MHz, DMSO-d6): d 400 MHz, DMSO-d6) d 8.45 - 8.39 (m, 2H), 8.08 (dt, J = 7.54, 1.59 Hz, 1H), 8.00 (dd, T= 7.77, 1.45 Hz, 1H), 7.96 - 7.89 (m, 4H), 7.61 (dtd, J = 21.70, 7.45, 1.59 Hz, 2H), 4.33 (s, 1H), 3.22 (s, 2H).

Reference： [1]Patent: WO2020/33782,2020,A1 .Location in patent: Paragraph 0291-0292

108
[ 2216-69-5 ]
[ 93-09-4 ]
(4-methoxynaphthalen-1-yl)(naphthalen-2-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With trifluoroacetic acid; trifluoroacetic anhydride at 20℃; for 12h;	4.1.2. General procedure for the synthesis of 4a-4u General procedure: Trifluoroacetic acid anhydride (TFAA, 2 mmol) was added to a solution of 1-methoxynaphthalene 2 (1.5 mmol) and various commercial available aromatic carboxylic acid (1 mmol) in Trifluoroacetic acid (TFA, 1 mL) and stirred at room temperature for 12 h. After the completion of the reaction, the solvent was removed under reduced pressure and the residue was purified by chromatography to give the desired products 4a-4u. Spectral data of all title compounds (4a-4u) were provided in Supplementary Material.

Reference： [1]Wang, Guangcheng; Liu, Wenjing; Tang, Juan; Ma, Xue; Gong, Zipeng; Huang, Yong; Li, Yongjun; Peng, Zhiyun [Bioorganic Chemistry, 2020, vol. 104]

109
[ 66003-76-7 ]
[ 93-09-4 ]
[ 3074-03-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	With palladium diacetate; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 110℃; Schlenk technique;

Reference： [1]An, Guoqiang; Wang, Limin; Han, Jianwei [Organic Letters, 2021, vol. 23, # 22, p. 8688 - 8693]

110
[ 150043-29-1 ]
[ 29978-83-4 ]
[ 93-09-4 ]
(2,3,3-trimethylbutan-2-ylcarbamoyl)(2-(prop-2-ynyloxy)phenyl)methyl 2-naphthoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: o-(prop-2-ynoxy)-benzaldehyde; naphthalene-2-carboxylate With tetrabutylammonium bromide In ethanol at 20℃; for 1h; Inert atmosphere; Stage #2: 1,1,3,3-tetramethylbutyl isocyanide In ethanol at 5 - 20℃; for 12h; Inert atmosphere;	3.2.1. General Procedure for the Synthesis of (2,3,3-trimethylbutan-2-ylcarbamoyl)(2-(prop-2-ynyloxy)phenyl)methyl substituted benzoate (Novel passeriniadducts) (4a-j) General procedure: In a 100 ml RBF equipped with a hot magnetic stirrerwith the septum, the mixture of aromatic acid (1) (0.01 mol),2-(prop-2-ynyloxy)benzaldehyde (2) (0.01 mol) and tetrabutyl ammonium bromide (TBAB) (10 mol%) was added inethanol as the solvent; the mixture was stirred at RT (roomtemperature) under nitrogen atmosphere for 1.0 h. The reactionmixture was cooled to 5-10 oC temperature and 2-isocyano-2,3,3-trimethylbutane (3) (0.012 mol) was addedhastily under the same reaction conditions. The reaction wasoptimized with or without PTC and is well discussed in theresults and discussion part (Table 1). It was stirred for a further12 h at RT conditions under TLC monitoring [hexane(4): ethyl acetate (6)]. After completion of the reaction, thesolvent was distilled off under vacuum and column chromatography(30% Ethyl acetate and 70% Hexane) was performedfor the purification of the product.A similar procedure was followed to obtain other diverse adducts (4a-j) (Reaction Scheme 1). All the synthesized molecules were confirmed by MS, IR, PMR, CMR, and elemental analysis.

Reference： [1]Jivani, Amita J.; Kapadiya, Khushal M.; Khunt, Ranjan C. [Letters in Organic Chemistry, 2022, vol. 19, # 4, p. 326 - 332]

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Technical Information

• Acids Combine with Acyl Halides to Produce Anhydrides • Acyl Chloride Hydrolysis • Amide Hydrolysis • Amide Hydrolysis • Anhydride Hydrolysis • Arndt-Eistert Homologation • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Carbonation of Organometallics • Carboxylate Salt Formation • Carboxylic Acids React with Alcohols to Form Esters • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conversion of Amino with Nitro • Decarboxylation of Substituted Propanedioic • Deprotection of Cbz-Amino Acids • Deprotonation of Methylbenzene • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Esters Hydrolyze to Carboxylic Acids and Alcohols • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Hunsdiecker-Borodin Reaction • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Nitration of Benzene • Nitriles Hydrolyze to Carboxylic Acids • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Aldehydes Furnishes Carboxylic Acids • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Oxidation of Primary Alcohols Furnishes Carboxylic Acids • Passerini Reaction • Peptide Bond Formation with DCC • Periodic Acid Degradation of Sugars • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Reduction of Carboxylic Acids by LiAlH4 • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Sulfonation of Benzene • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Conversion of Carboxylic Acids into Acyl Halides • The Nitro Group Conver to the Amino Function • Ugi Reaction • Vilsmeier-Haack Reaction

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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 93-09-4 ] {[proInfo.proName]}

Quality Control of [ 93-09-4 ]

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Product Details of [ 93-09-4 ]

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[ 93-09-4 ] Synthesis Path-Upstream 1~9

[ 93-09-4 ] Synthesis Path-Downstream 1~110

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Aryls

Carboxylic Acids

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[ 93-09-4 ]

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[ 93-09-4 ]