[ CAS No. 574-96-9 ]

Name: 574-96-9|1-Hydroxy-2-naphthaldehyde|98%
Brand: Ambeed
SKU: A308182
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Quality Control of [ 574-96-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 574-96-9 ]

Product Details of [ 574-96-9 ]

CAS No. :	574-96-9	MDL No. :	MFCD00092325
Formula :	C₁₁H₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OITQDWKMIPXGFL-UHFFFAOYSA-N
M.W :	172.18	Pubchem ID :	443195
Synonyms :

Calculated chemistry of [ 574-96-9 ]

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 :	51.36
TPSA :	37.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.44
Log Po/w (XLOGP3) :	2.55
Log Po/w (WLOGP) :	2.36
Log Po/w (MLOGP) :	1.82
Log Po/w (SILICOS-IT) :	2.64
Consensus Log Po/w :	2.16

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.02
Solubility :	0.165 mg/ml ; 0.000961 mol/l
Class :	Soluble
Log S (Ali) :	-2.98
Solubility :	0.18 mg/ml ; 0.00105 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 :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 574-96-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 574-96-9 ]

* 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 [ 574-96-9 ]
Downstream synthetic route of [ 574-96-9 ]

[ 574-96-9 ] Synthesis Path-Upstream 1~3

1
[ 60859-75-8 ]
[ 574-96-9 ]
[ 617-36-7 ]
[ 74222-20-1 ]
[ 88472-35-9 ]

Reference： [1] Chemical & Pharmaceutical Bulletin, 1983, vol. 31, p. 2944 - 2947
[2] Chemical & Pharmaceutical Bulletin, 1983, vol. 31, p. 2944 - 2947

2
[ 60859-75-8 ]
[ 574-96-9 ]
[ 617-36-7 ]
[ 74222-18-7 ]
[ 88472-35-9 ]

Reference： [1] Chemical & Pharmaceutical Bulletin, 1983, vol. 31, p. 2944 - 2947

3
[ 60859-75-8 ]
[ 574-96-9 ]
[ 617-36-7 ]
[ 74222-20-1 ]
[ 74222-18-7 ]
[ 88472-35-9 ]

Reference： [1] Chemical & Pharmaceutical Bulletin, 1983, vol. 31, p. 2944 - 2947

[ 574-96-9 ] Synthesis Path-Downstream 1~69

1
[ 574-96-9 ]
[ 7469-77-4 ]

Reference： [1]Journal of the Indian Chemical Society,1959,vol. 36,p. 76,80

2
[ 60859-75-8 ]
[ 574-96-9 ]
[ 617-36-7 ]
[ 74222-20-1 ]
[ 74222-18-7 ]
[ 88472-35-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1983,vol. 31,p. 2944 - 2947

3
[ 60859-75-8 ]
[ 574-96-9 ]
[ 617-36-7 ]
[ 74222-20-1 ]
[ 88472-35-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1983,vol. 31,p. 2944 - 2947
[2]Chemical and pharmaceutical bulletin,1983,vol. 31,p. 2944 - 2947

4
[ 60859-75-8 ]
[ 574-96-9 ]
[ 617-36-7 ]
[ 74222-18-7 ]
[ 88472-35-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1983,vol. 31,p. 2944 - 2947

5
[ 574-96-9 ]
[ 106-95-6 ]
[ 135522-20-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 2h;	General procedure: A solution of salicylaldehyde (5 mmol) in dry DMF (10.0 mL) was treated with K2CO3 (7.0 mmol) and allyl bromide (6.0 mmol). The mixture was stirred 2 h at 70 C. Then it was cooled to room temperature and poured into saturated aqueous NH4Cl and extracted 4 times with EtOAc. The organic phases were evaporated and then subjected to column chromatography to afford the starting materials 1.

Reference： [1]Tetrahedron,1991,vol. 47,p. 4007 - 4030
[2]Journal of the American Chemical Society,2009,vol. 131,p. 14190 - 14191
[3]Journal of Organic Chemistry,1998,vol. 63,p. 864 - 866
[4]Chemical Communications,2016,vol. 52,p. 4179 - 4182
[5]Organic Letters,2019,vol. 21,p. 1388 - 1392
[6]Tetrahedron,2019,vol. 75

6
[ 50493-10-2 ]
[ 574-96-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With aluminum (III) chloride; In dichloromethane; for 2h;	A suspension ofanhydrous AlCl3 (2 g, powder) in DCM (10 ml) was stirred at room temperature for 2 h. The 1-methoxy-2-naphthaldehyde (1 g) in DCM (10 ml) was added and stirred for 2 h. The mixture was poured in dilute HCl and extracted with chloroform. The organic layer was concentrated and purified on column chromatography over silica gel in 15% ethyl acetate / hexane to give the 1-hydroxy- 2-naphthaldehyde (0.8 g, 90%). 1H NMR (CDCl3, 500 MHz) d 7.36 (d, J = 8.1 Hz), 7.47 (d, J =8.6 Hz, 1H), 7.54 (m, 1H), 7.64 (m, 1H), 7.77 (d, 8.1 Hz, 1H), 8.42 (m, 1H),9.95 (s, 1H), 12.66 (s, 1H)].

Reference： [1]Journal of Chemical Research, Miniprint,2003,p. 857 - 868
[2]Journal of Chemical Research,2010,p. 222 - 227
[3]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2015,vol. 143,p. 72 - 80
[4]Tetrahedron,1975,vol. 31,p. 1005 - 1009

7
[ 574-96-9 ]
[ 77-76-9 ]
2,4-dimethoxy-2-methyl-3,4-dihydro-2<i>H</i>-benzo[<i>h</i>]chromene [ No CAS ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 7943 - 7946
[2]Journal of the Chemical Society. Perkin Transactions 1 (2001),2000,p. 3082 - 3084

8
(1S)-1-(β-naphthylmethyl)-1,2-ethylenediamine [ No CAS ]
[ 574-96-9 ]
N,N'-bis(1'-hydroxy-2'-naphtylidene)-(1S)-(β-naphthylmethyl)-1,2-ethylenediamine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 8610 - 8611
[2]Angewandte Chemie - International Edition,2007,vol. 46,p. 7010 - 7014

9
[ 574-96-9 ]
[ 62779-70-8 ]
N,N'-bis(1'-hydroxy-2'-naphthylidene)-(1S)-phenyl-1,2-ethylenediamine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 8610 - 8611

10
[ 574-96-9 ]
[ 85612-60-8 ]
N,N'-bis(1'-hydroxy-2'-naphthylidene)-(1S)-benzyl-1,2-ethylenediamine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 8610 - 8611

11
[ 6872-17-9 ]
[ 574-96-9 ]
(+/-)-5'-chloro-1',3',3'-trimethylspiro(indoline-2',2-2H-naphtho[1,2-b]pyran) [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 1037 - 1045

12
[ 574-96-9 ]
[ 75-36-5 ]
[ 86896-20-0 ]

Yield	Reaction Conditions	Operation in experiment
900 mg	With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 1h;	To a stirred solution of l-hydroxy-2-naphthaldehyde (1.89 g, 10.46 mmol) in DCM (15 inL) was added triethylamine (1.89 mL, 13.60 mmol) at room temperature. The resulting mixture was cooled to 0 C and acetyl chloride (1.26 mL, 17.79 mmol) was added followed by the addition of DMAP (127 mg, 1.0 mmol) and stirred for 1 hr at room temperature. Reaction mixture was diluted with DCM (200 mL), washed with water, followed by brine, dried over sodium sulfate and was concentrated under reduced pressure to afford crude which was purified by column chromatography using silica (100-200 mesh) and EtOAc-hexane as eluent to afford 2-formylnaphthalen-l-yl acetate (900 mg) as yellow solid.

Reference： [1]Journal of Chemical Research,2006,p. 688 - 690
[2]Patent: WO2014/141110,2014,A2 .Location in patent: Page/Page column 87

13
[ 4319-49-7 ]
[ 574-96-9 ]
4-[(1-hydroxy-2-naphthylmethylen)amino]morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In methanol; ethanol; at 20℃;	General procedure: To a solution of the amine (2.90 mmol) in ethanol (10 mL) was slowly added a solution of the corresponding aldehyde (2.90 mmol) in a small volume of methanol. The mixture was stirred at room temperature giving rise to a precipitate within a few minutes. When the mixture did not precipitate spontaneously, it was evaporated in vacuum and gave a solid on standing or on cooling. The resulting product was collected by filtration, washed successively with cold water, ethanol, and diethyl ether, and recrystallized from ethanol or methanol.

Reference： [1]Tetrahedron,2011,vol. 67,p. 2025 - 2034
[2]Mendeleev Communications,2009,vol. 19,p. 141 - 143

14
[ 73220-21-0 ]
[ 574-96-9 ]

Yield	Reaction Conditions	Operation in experiment
650 mg	With chloro-trimethyl-silane; sodium iodide; In acetonitrile; at 0 - 20℃; for 3h;	To a stirred solution of l-(methoxymethoxy)naphthalene (2.2 g, 10.185 mmol) in acetonitrile (15 mL) was added sodium iodide (3.05 g, 20.370 mmol) at room temperature. Resulting mixture was cooled to 0 C, TMSC1 (1.93 mL, 15.277 mmol) was added drop wise and stirred for 3 hrs at room temperature. Reaction mixture was concentrated under reduced pressure and dissolved in DCM (250 mL). The organic layer was washed with brine solution, dried over sodium sulfate and was concentrated under reduced pressure to afford crude product which was purified by column chromatography using silica (100-200 mesh) and EtOAc-hexane as eluent to afford 1- hydroxy-2-naphthaldehyde (650 mg) of as off white solid.

Reference： [1]Organic Letters,2010,vol. 12,p. 2202 - 2205
[2]Organic Letters,2010,vol. 12,p. 1732 - 1735
[3]Journal of the American Chemical Society,2013,vol. 135,p. 3964 - 3970
[4]Patent: WO2014/141110,2014,A2 .Location in patent: Page/Page column 86; 87

15
[ 574-96-9 ]
[ 137-07-5 ]
[ 76995-70-5 ]

Yield	Reaction Conditions	Operation in experiment
55%	In 1,4-dioxane; at 100℃; for 12h;Increased pressure;	Preparation Example 21; Preparation of Compound (21); In 1,4-dioxane (28 mL, 2.1 M), dissolved were 2-aminobenzenethiol (8.7 g, 69.6 mmol) and 1-hydroxy-2-naththalaldehyde (10.0 g, 58 mmol), and the solution was stirred at 100 C. under pressure for 12 hours. After cooling to room temperature, the reaction mixture was extracted with MC (150 mL), washed with water (100 mL) and dried under reduced pressure. Purification via silica gel column chromatography (n-hexane: MC=3:1) gave 2-(benzo[d]thiazol-2-yl)naphthalen-1-ol (8.9 g, 32 mmol, 55%).Compound (21) (1.5 g, 1.6 mmol, 67%) was obtained by repeating the same procedure as described in Preparation Example 1, but using 2-(benzo[d]thiazol-2-yl)naphthalen-1-ol (2.0 g, 7.2 mmol), ZnCl2 (477.1 mg, 4.8 mmol), EtOH (120 mL, 0.02 M), NH4OH (2.0 mL) and water (20 mL).mp. >300 C.1H NMR (300 MHz, CDCl3): d=8.23-8.1 (m, 3H), 7.7-7.5 (m, 3H), 7.4-7.3 (m, 4H)MS/FAB: 956 (found), 956.78 (calculated)

Reference： [1]Patent: US2010/152455,2010,A1 .Location in patent: Page/Page column 14

16
[ 574-96-9 ]
[ 106-96-7 ]
[ 1271773-34-2 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 964 - 967
[2]Chemistry - A European Journal,2011,vol. 17,p. 1437 - 1441
[3]Heterocycles,2018,vol. 96,p. 42 - 49

17
[ 6928-85-4 ]
[ 574-96-9 ]
1-[(1-hydroxy-2-naphthylmethylen)amino]-4-methylpiperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	In methanol; ethanol; at 20℃;	General procedure: To a solution of the amine (2.90 mmol) in ethanol (10 mL) was slowly added a solution of the corresponding aldehyde (2.90 mmol) in a small volume of methanol. The mixture was stirred at room temperature giving rise to a precipitate within a few minutes. When the mixture did not precipitate spontaneously, it was evaporated in vacuum and gave a solid on standing or on cooling. The resulting product was collected by filtration, washed successively with cold water, ethanol, and diethyl ether, and recrystallized from ethanol or methanol.

Reference： [1]Tetrahedron,2011,vol. 67,p. 2025 - 2034

18
[ 574-96-9 ]
[ 2213-43-6 ]
[ 1290140-27-0 ]

Yield	Reaction Conditions	Operation in experiment
25%	In methanol; ethanol; at 20℃;	General procedure: To a solution of the amine (2.90 mmol) in ethanol (10 mL) was slowly added a solution of the corresponding aldehyde (2.90 mmol) in a small volume of methanol. The mixture was stirred at room temperature giving rise to a precipitate within a few minutes. When the mixture did not precipitate spontaneously, it was evaporated in vacuum and gave a solid on standing or on cooling. The resulting product was collected by filtration, washed successively with cold water, ethanol, and diethyl ether, and recrystallized from ethanol or methanol.

Reference： [1]Tetrahedron,2011,vol. 67,p. 2025 - 2034

19
[ 574-96-9 ]
[ 61147-58-8 ]
2,6-dimethyl-1-[(1-hydroxy-2-naphthylmethylen)amino]piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	In methanol; ethanol; at 20℃;	General procedure: To a solution of the amine (2.90 mmol) in ethanol (10 mL) was slowly added a solution of the corresponding aldehyde (2.90 mmol) in a small volume of methanol. The mixture was stirred at room temperature giving rise to a precipitate within a few minutes. When the mixture did not precipitate spontaneously, it was evaporated in vacuum and gave a solid on standing or on cooling. The resulting product was collected by filtration, washed successively with cold water, ethanol, and diethyl ether, and recrystallized from ethanol or methanol.

Reference： [1]Tetrahedron,2011,vol. 67,p. 2025 - 2034

20
[ 574-96-9 ]
[ 188120-06-1 ]
[ 1311229-21-6 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 3706 - 3709

21
[ 574-96-9 ]
[ 36267-33-1 ]
[ 1346518-74-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	In ethanol at 20℃; for 8h; Inert atmosphere;

Reference： [1]Van Leeuwen, Piet W. N. M.; Rivillo, David; Raynal, Matthieu; Freixa, Zoraida [Journal of the American Chemical Society, 2011, vol. 133, # 46, p. 18562 - 18565]

22
[ 574-96-9 ]
[ 604-59-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 1.5 h / -78 - 0 °C / Inert atmosphere 1.3: 0 °C 2.1: manganese(IV) oxide / acetone / 24 h / 20 °C / Inert atmosphere 3.1: dmap / N,N-dimethyl-formamide / 2 h / 0 - 30 °C / Inert atmosphere

Reference： [1]Yoshida, Masahito; Fujino, Yuta; Saito, Koya; Doi, Takayuki [Tetrahedron, 2011, vol. 67, # 51, p. 9993 - 9997]

23
[ 574-96-9 ]
[ 536-74-3 ]
C₁₉H₁₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of phenylacetylene derivative 5 (2.2 equiv) in dry THF (4 mL/mmol) was added BuLi (1.60 M in hexane solution, 2.2 equiv) dropwise at -78 C under argon. After stirring at the same temperature for 1 h, a solution of aldehyde 4 in dry THF (1 mL/mmol) was added to the reaction mixture dropwise at -78 C under argon. After being stirred at the same temperature for 1 h and at 0 C for additional 30 min, the reaction mixture was quenched with saturated aqueous NH4Cl at 0 C. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with saturated aqueous NaHCO3, brine, dried over MgSO4, and filtered. The filtrate was concentrated in vacuo to afford the propargylic alcohol. The crude alcohol was used for the next reaction without further purification.To a solution of the crude alcohol in acetone (1 mL/mmol) was added MnO2 (5 equiv) at room temperature under argon. After being stirred at the same temperature, the reaction mixture was filtered through a pad of Celite and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel to afford o-alkynoylphenol derivatives 3. Alkynoylphenols 6 were also prepared in a similar manner. Spectral data of 3a-3p and 6a-6c have been reported previously10.

Reference： [1]Tetrahedron,2011,vol. 67,p. 9993 - 9997

24
[ 574-96-9 ]
[ 63139-21-9 ]
[ 118-92-3 ]
[ 1370731-98-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	In tetrachloromethane; for 0.05h;Microwave irradiation;	General procedure: A mixture of 2-aminobenzoic acid (0.137 g, 1 mmol), 2-hydroxy-3-methoxybenzaldehyde (0.152 g, 1 mmol), and phenylboronic acid (0.122 g, 1 mmol) in CCl4 (4 mL) was irradiated for 3 min at 450 W. TLC showed completion of the reaction. After cooling to room temperature, the solid precipitate was filtered, washed with CCl4 (2×3 mL). The product was obtained by recrystallization from DMSO.

Reference： [1]Tetrahedron,2012,vol. 68,p. 3377 - 3383

25
[ 574-96-9 ]
[ 638-07-3 ]
[ 1384518-82-4 ]

Yield	Reaction Conditions	Operation in experiment
42%	With piperidine; In dichloromethane; at 20℃; for 8h;	General procedure: Ethyl 4-chloro-3-oxobutanoate (164 mg, 1 mmol) was added to the mixture of a stirred solution of 5-fluoro-2-hydroxybenzaldehyde (140 mg, 1 mmol) and piperidine (30 mol%) in DCM (2 mL) at room temperature over a period of 15 min. The mixture was stirred for another 8 h at the same temperature. After completion of the reaction (TLC), the crude product was subjected to column chromatography purification (hexane/ethyl acetate 95:5) to give 2e (183 mg, 64% yield) as yellow liquid.

Reference： [1]Tetrahedron,2012,vol. 68,p. 6289 - 6297

26
[ 574-96-9 ]
[ 5164-76-1 ]
[ 1395923-92-8 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 8028 - 8037,10

27
[ 578-66-5 ]
[ 574-96-9 ]
[ 1141898-51-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	In ethanol; at 20℃;Inert atmosphere;	0.18 g (1.1 mmol) of 8-quinolineamine and 0.18 g of <strong>[574-96-9]1-hydroxynaphthalene-2-carbaldehyde</strong>(1 mmol) was dissolved in purified ethanol (10 mL).The reaction solution was heated and stirred under a nitrogen atmosphere for one hour. Thereafter, the reaction solution was cooled to room temperature, filtered and recrystallized with ethanol to obtain a red product. The reaction formula is as follows. Yield: 88%.

Reference： [1]Patent: KR101548806,2015,B1 .Location in patent: Paragraph 0029; 0030; 0031; 0032; 0033; 0034
[2]Bulletin of the Chemical Society of Japan,2012,vol. 85,p. 1210 - 1221
[3]Inorganic Chemistry Communications,2013,vol. 33,p. 48 - 51

28
[ 574-96-9 ]
[ 2834-92-6 ]
1-[(1-hydroxynaphthalen-2-yl)methylidene]amino}naphthalen-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77.6%	In ethanol; at 20℃; for 2h;	A solution of 1-amino-2-naphthol hydrochloride (0.22 g, 1.1 mmol) in ethanol was added to a solution containing <strong>[574-96-9]1-hydroxynaphthalene-2-carbaldehyde</strong> (0.18 g, 1 mmol) in ethanol. The reaction mixture was stirred for 2 h at room temperature until a dark red precipitate appeared. The resulting precipitate was filtered and washed 2 times with ice methanol. The yield: 0.26 g (77.6 %). 1H NMR (DMSO-d6, 400 MHz) delta: 15.69 (d, 1H), 10. 25 (s, 1H), 9.12 (d, 1H), 8.49 (d, 1H), 8.15 (d, 1H), 7.91 (d, 1H), 7.74 (m, 2H), 7.64 (m, 2H), 7.54 (t, 1H), 7.42 (m, 3H), 7.14 (d, 1H). 13C NMR (DMSO-d6, 400 MHz): delta 171.08, 163.64, 146.84, 136.69, 129.98, 128.54, 128.38, 128.27, 128.00, 127.81, 127.49, 125.25, 124.42, 123.63, 121.67, 120.44, 118.92, 115.61, 110.57 ppm. HRMS (ESI): m/z calcd for C21H15NO2+Na+: 336.1 [M+Na+]: found, 335.87. Anal. Calcd for C21H15NO2 (313.35): C, 80.49; H, 4.82; N, 4.47. Found: C, 80.60; H, 5.30; N, 4.70%.

Reference： [1]Dyes and Pigments,2013,vol. 99,p. 6 - 13

29
[ 574-96-9 ]
[ 1385073-65-3 ]
diethyl (N'-4-((1-hydroxynaphthalen-2-yl)methylene)-2-phenoxyacetohydrazide)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In ethanol; at 80℃; for 8h;	General procedure: To a clear solution of 3 (0.5 g, 1.2 mmol) in ethanol (10 mL), 1.2 mmol of aldehyde/ketone was added and refluxed for 8 h. Catalytic amount (0.2 mL) of glacial acetic acid was used for the synthesis of 5a-h. Resulting solid was filtered, washed with ethanol and finally recrystallized with methanol/chloroform mixture. The characterization and spectral data of final compounds are given below.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 70,p. 341 - 349

30
[ 574-96-9 ]
[ 90965-06-3 ]
[ 74-88-4 ]
[ 1172134-59-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium hydride; potassium carbonate; In methanol;	The structure, purity, and heme-activating properties of '882 were verified following itsresynthesis by way of a five-step reaction sequence starting from commercially available <strong>[574-96-9]1-hydroxy-2-naphthaldehyde</strong> ( 44 ).

Reference： [1]Patent: WO2014/18925,2014,A1 .Location in patent: Paragraph 0099; 00100

31
[ 88-21-1 ]
[ 574-96-9 ]
[ 1564243-10-2 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol;	3.1 Synthesis and characterization of H2L and 1 The new Schiff base (E)-2-(((1-hydroxynaphthalen-2-yl)methylene)amino)benzenesulfonic acid (H2L) was prepared by reaction of 2-aminobenzenesulfonic acid with 1-hydroxy-2-naphthaldehyde in methanol (see Electronic Supplementary Information). Greenish-black crystals of complex [Cu(H2R)(HL)]?H2O (1,

Reference： [1]Catalysis Communications,2014,vol. 48,p. 69 - 72

32
[ 574-96-9 ]
[ 1671-88-1 ]
3,5-bis(2-pyridyl)-4-[(1-hydroxy-2-naphthylmethylene)amino]-[4H]-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In methanol; ethanol; for 24h;Reflux;	General procedure: To a solution of the amine (2.90 mmol) in ethanol (10 mL) was slowly added a solution of the corresponding aldehyde (2.90 mmol) in methanol (2 mL). The mixture was refluxed for 24 h and then cooled at room temperature. When a solid did not precipitate, the reaction mixture was evaporated under reduced pressure and gave rise to a solid on standing or on cooling. The resulting product was isolated by filtration, washed successively with cold water, ethanol, and diethyl ether, and recrystallized from ethanol or methanol.

Reference： [1]Tetrahedron,2014,vol. 70,p. 2319 - 2329

33
[ 574-96-9 ]
[ 105-36-2 ]
[ 74222-20-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium carbonate; In acetonitrile; for 15h;Reflux;	Ethyl Naphtho[1,2-b]furan-2-carboxylate (2) To a solution of <strong>[574-96-9]1-hydroxy-2-naphthaldehyde</strong> (1, 100 mg, 0.58 mmol)and ethyl bromoacetate (98 mg, 0.69 mmol) in acetonitrile (3 mL) was added potassium carbonate (161 mg, 1.16 mmol). After being stirred at reflux for 1.5 h, the mixture was diluted with water (20 mL), and extracted with ethyl acetate (50 mL). The organic layer was dried over anhydrous sodium sulfateand concentrated in vacuo, giving a residue that was subjected to column chromatography on silica gel (ethyl acetate-nhexane1 : 10) to obtain 100 mg (76%) of the title compound. 1H-NMR (300 MHz, CDCl3) delta: 8.47 (d, J=8.4 Hz, 1H), 7.93 (d,J=8.4 Hz, 1H), 7.53-7.73 (m, 5H), 4.46 (q, J=7.1 Hz, 2H), 1.46 (t, J=7.1 Hz, 3H).

Reference： [1]Chemical and Pharmaceutical Bulletin,2013,vol. 61,p. 1239 - 1247

34
[ 50-00-0 ]
[ 90-15-3 ]
[ 574-96-9 ]

Yield	Reaction Conditions	Operation in experiment
70%		General procedure: A aromatic Phenol 1 (0.1 mol), magnesiummethoxide (5 gr ), and the mixture was grindingto 1 minute at room temperature. A slurry ofparaformaldehyde powder6 (4 gr) in under grindingwas added in small portions over 2 min to thereaction mixture. Stirring was continued at r.t for 8min, after which added slowly to 10% sulfuric acid(20 ml g). The resulting mixture was stirred for 10min, after which the aqueous layer was separatedand extracted with ethyl acetate (2 × 100 ml). Thecombined organic layers and extracts were washedwith 10% sulfuric acid (20 ml) and water (20 ml)and evaporated under reduced pressure to give thesalicyaldehyde 3.
33%	With triethylamine; magnesium chloride; In acetonitrile; for 15h;Reflux;	1-Hydroxy-2-naphthaldehyde (1) To a solution of naphthalene-1-ol (2.0 g, 13.89 mmol) and paraformaldehyde(2.4 g, 83.34 mmol) in acetonitrile (50 mL) were added magnesium chloride (1.98 g, 20.8 mmol) and triethylamine (7.2 mL, 51.4 mmol). After being stirred at reflux for 15 h, the mixture was diluted with water (50 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with water and 5% aqueous hydrogen chloride solution, dried over anhydrous sodium sulfate, and concentrated in vacuo, giving a residue that was subjected to column chromatography on silica gel (ethyl acetate-n-hexane 1 : 10) to obtain 800 mg (33%) of the title compound. 1H-NMR (300 MHz, CDCl3) delta: 12.67 (s, 1H), 9.97 (s, 1H), 8.44 (d, J=8.4 Hz, 1H), 7.79 (d, J=8.4 Hz, 1H), 7.66 (dd, J=8.4, 8.1 Hz, 1H) 7.55 (dd, J=8.4, 8.1 Hz, 1H), 7.49(d, J=8.6 Hz, 1H), 7.37 (d, J=8.6 Hz, 1H).

Reference： [1]Oriental Journal of Chemistry,2013,vol. 29,p. 1611 - 1614
[2]Journal of Organic Chemistry,2017,vol. 82,p. 5663 - 5668
[3]Luminescence,2018,vol. 33,p. 29 - 33
[4]Chemical and Pharmaceutical Bulletin,2013,vol. 61,p. 1239 - 1247

35
[ 123-91-1 ]
[ 574-96-9 ]
[ 1581231-24-4 ]

Yield	Reaction Conditions	Operation in experiment
27%	With tert.-butylhydroperoxide; copper(l) chloride; In water; at 100℃;	General procedure: To a flask charged with a stir bar, 1a (25.0 mg, 0.20 mmol, 1.0 equiv), CuCl (1.0 mg, 0.01 mmol, 0.05 equiv), TBHP (0.059 mL, 0.61 mmol, 70 wt % in water, 3.0 equiv), and 1,4-dioxane as ether (2.0 mL, 22.8 mmol, 112.0 equiv) were mixed at room temperature. The reaction temperature was increased to 100C and the reaction mixture was stirred for 15-90 min. The reaction mixture was cooled to room temperature and the solvent was removed under vacuum yielding the crude product, which was purified by flash chromatography (ethyl acetate/hexane, 2:8) to afford the required product 3a.

Reference： [1]Organic Letters,2014,vol. 16,p. 1912 - 1915
[2]Tetrahedron,2015,vol. 71,p. 2290 - 2297

36
[ 574-96-9 ]
[ 372-31-6 ]
[ 1609100-36-8 ]

Yield	Reaction Conditions	Operation in experiment
68%	With L-proline/SiO2; at 80℃; for 0.233333h;Microwave irradiation; Sealed tube;	General procedure: Oven Heating ProcedureIn a typical experiment of Knoevenagel condensation reaction catalyzed by immobillized L-proline,aldehyde (7 mmol), ethyl trifluoroacetoacetate (14 mmol) and 4.5 g of L-proline/SiO2 were thoroughlyground in a mortar. The mixture was charged in a microwave tube (capacity 10 mL), then sealed withpolytetrafluoroethylene film and heated in an oven at 80 C for 6-8 h (monitored by HPLC). Themixture was allowed to cool to room temperature. Ethyl acetate was added and the resulting mixturewas filtered, and the residue was sequentially washed with ethyl acetate or dichloromethane for at leastthree times. The combined solution was evaporated under reduced pressure, and the crude product wasrecrystallized from ethanol or ethyl acetate.

Reference： [1]Molecules,2013,vol. 18,p. 11964 - 11977

37
[ 574-96-9 ]
[ 68471-55-6 ]
(7R,7aR,10aS)-10-benzoyl-7-hydroxyl-7,7a,8,9,10,10a-hexahydrobenzo[7,8]chromeno[2,3-b]pyrrole [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 6039 - 6049
[2]Organic Letters,2014,vol. 16,p. 5972 - 5975

38
[ 2033-24-1 ]
[ 574-96-9 ]
[ 37660-22-3 ]
C₁₉H₁₇N₃O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With [gamma-Fe2O3-encapsulated-HAp-SO3H]; at 60℃; for 0.0833333h;	General procedure: [gamma-Fe2O3Hap-SO3H] was synthesized according to the procedures reported in Ref. [2]. Then to a mixture of 6-amino-2-(methylthio or ethylthio)pyrimidin-4(3H)-one (1 mmol), Meldrum?s acid (1 mmol) and aryl aldehydes (1 mmol) was added [gamma-Fe2O3Hap-SO3H] (10 mg, 0.9 mol%) and the reaction mixture was stirred mechanically at 60 C. After the completion of the reaction, which was monitored by TLC analysis, the reaction mixture was diluted with hot ethanol and the catalyst was easily separated from the reaction mixture by an external magnet. The product obtained was collected by filtration, washed with ethanol and recrystallized from appropriate solvent to furnish the desired pure product (4a-n).

Reference： [1]Chinese Chemical Letters,2014,vol. 25,p. 1387 - 1391

39
[ 574-96-9 ]
[ 53703-63-2 ]
C₁₉H₁₈N₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With acetic acid; In ethanol; at 75℃; for 72h;	General procedure: General procedure: 8-Hydrazinocaffeine (3) (112 mg;0.5 mmol) and carbonyl compound (1 mmol; 2 eq.) were mixedin ethanol (20 mL, containing 0.2 mL of acetic acid) and heated at 75 omicronC for 3 days. After cooling down, reaction mixture was evaporatedto dryness and solid residue was suspended in diethyl ether(50 mL), filtered off, washed with additional portion of diethylether (3 25 mL) and dried in vacuo at 50 C to obtain the hydrazone.

Reference： [1]Bioorganic Chemistry,2015,vol. 60,p. 19 - 29

40
[ 110-71-4 ]
[ 574-96-9 ]
1-(1,2-dimethoxyethoxy)-2-naphthaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With tert.-butylhydroperoxide; copper(l) chloride; In water; at 100℃;	General procedure: To a flask charged with a stir bar, 1a (25.0 mg, 0.20 mmol, 1.0 equiv), CuCl (1.0 mg, 0.01 mmol, 0.05 equiv), TBHP (0.059 mL, 0.61 mmol, 70 wt % in water, 3.0 equiv), and 1,4-dioxane as ether (2.0 mL, 22.8 mmol, 112.0 equiv) were mixed at room temperature. The reaction temperature was increased to 100C and the reaction mixture was stirred for 15-90 min. The reaction mixture was cooled to room temperature and the solvent was removed under vacuum yielding the crude product, which was purified by flash chromatography (ethyl acetate/hexane, 2:8) to afford the required product 3a.

Reference： [1]Tetrahedron,2015,vol. 71,p. 2290 - 2297

41
[ 574-96-9 ]
[ 100-58-3 ]
2-(hydroxy(phenyl)methyl)naphthol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 20℃; for 1h;Inert atmosphere; Schlenk technique;	General procedure: Under N2, a solution of 2-hydroxybenzaldehyde 5 (3.0 mmol) in tetrahydrofuran (10 mL)was added to a solution of Grignard reagent 6 (9.0 mmol), the mixture was stirred at roomtemperature for 1 hour. The reaction mixture was quenched by saturated ammonium chloride (20mL) and extracted with dichloromethane (40 mL×3). Then the combined organic layer was driedby anhydrous sodium sulfate, concentrated in vacuo. A short silica gel column filtration of thecrude mixture afforded 2-hydroxyalkylphenols 7

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4334 - 4338
[2]Chinese Journal of Chemistry,2014,vol. 32,p. 981 - 984
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 3689 - 3693
Angew. Chem.,2017,vol. 129,p. 3743 - 3747,5
[4]Chemical Communications,2017,vol. 53,p. 3531 - 3534
[5]Angewandte Chemie - International Edition,2017,vol. 56,p. 4006 - 4010
Angew. Chem.,2017,vol. 129,p. 4064 - 4068,5
[6]Organic Letters,2018,vol. 20,p. 1158 - 1161

42
[ 932-31-0 ]
[ 574-96-9 ]
C₁₈H₁₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 20℃; for 1h;Inert atmosphere; Schlenk technique;	General procedure: Under N2, a solution of 2-hydroxybenzaldehyde 5 (3.0 mmol) in tetrahydrofuran (10 mL)was added to a solution of Grignard reagent 6 (9.0 mmol), the mixture was stirred at roomtemperature for 1 hour. The reaction mixture was quenched by saturated ammonium chloride (20mL) and extracted with dichloromethane (40 mL×3). Then the combined organic layer was driedby anhydrous sodium sulfate, concentrated in vacuo. A short silica gel column filtration of thecrude mixture afforded 2-hydroxyalkylphenols 7

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4334 - 4338
[2]Chemical Communications,2017,vol. 53,p. 3531 - 3534
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 4006 - 4010
Angew. Chem.,2017,vol. 129,p. 4064 - 4068,5

43
[ 574-96-9 ]
[ 28987-79-3 ]
C₁₈H₁₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 20℃; for 1h;Inert atmosphere; Schlenk technique;	General procedure: Under N2, a solution of 2-hydroxybenzaldehyde 5 (3.0 mmol) in tetrahydrofuran (10 mL)was added to a solution of Grignard reagent 6 (9.0 mmol), the mixture was stirred at roomtemperature for 1 hour. The reaction mixture was quenched by saturated ammonium chloride (20mL) and extracted with dichloromethane (40 mL×3). Then the combined organic layer was driedby anhydrous sodium sulfate, concentrated in vacuo. A short silica gel column filtration of thecrude mixture afforded 2-hydroxyalkylphenols 7

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4334 - 4338
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 3689 - 3693
Angew. Chem.,2017,vol. 129,p. 3743 - 3747,5
[3]Chemical Communications,2017,vol. 53,p. 3531 - 3534
[4]Angewandte Chemie - International Edition,2017,vol. 56,p. 4006 - 4010
Angew. Chem.,2017,vol. 129,p. 4064 - 4068,5

44
[ 574-96-9 ]
[ 4294-57-9 ]
C₁₈H₁₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 20℃; for 1h;Inert atmosphere; Schlenk technique;	General procedure: Under N2, a solution of 2-hydroxybenzaldehyde 5 (3.0 mmol) in tetrahydrofuran (10 mL)was added to a solution of Grignard reagent 6 (9.0 mmol), the mixture was stirred at roomtemperature for 1 hour. The reaction mixture was quenched by saturated ammonium chloride (20mL) and extracted with dichloromethane (40 mL×3). Then the combined organic layer was driedby anhydrous sodium sulfate, concentrated in vacuo. A short silica gel column filtration of thecrude mixture afforded 2-hydroxyalkylphenols 7

45
[ 574-96-9 ]
[ 352-13-6 ]
C₁₇H₁₃FO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 20℃; for 1h;Inert atmosphere; Schlenk technique;	General procedure: Under N2, a solution of 2-hydroxybenzaldehyde 5 (3.0 mmol) in tetrahydrofuran (10 mL)was added to a solution of Grignard reagent 6 (9.0 mmol), the mixture was stirred at roomtemperature for 1 hour. The reaction mixture was quenched by saturated ammonium chloride (20mL) and extracted with dichloromethane (40 mL×3). Then the combined organic layer was driedby anhydrous sodium sulfate, concentrated in vacuo. A short silica gel column filtration of thecrude mixture afforded 2-hydroxyalkylphenols 7

46
[ 574-96-9 ]
[ 6325-92-4 ]
C₂₄H₁₉NOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
Ca. 100%	In ethanol; at 20℃; for 0.5h;	2-(Benzylthio)aniline (0.215 g, 1 mmol) was dissolved in ethanol. To the above solution, anethanolic solution of 2-hydroxynaphthaldehyde (0.172 g, 1 mmol) was added dropwise withcontinuous stirring. The resulting solution was allowed to stir for 30 min at room temperature.The color of the solution changed to dark yellow. The solution was kept at 0 C for 4 h;a yellow crystalline product formed, was filtered off, washed with 25% ethanol-water, anddried in vacuum (10-2 torr). The product was recrystallized in ethanol, giving suitable crystalsfor single crystal X-ray diffraction analysis. Yield was almost quantitative. m.p.: 185 C.IR (KBr, cm-1) 3435 (m), 1610 (s), 1457 (s), 1167 (s), 743 (s). 1H-NMR (CDCl3, 300 MHz):delta 15.30 (1H, s, OH), 9.2 (1H, s, CH=N), 7.1-8.09 (12H, m, Ar-H), 4.1 (2H, s, CH2). UV-vis [DMF, lambdamax, nm (epsilonmax, M-1 cm-1)]: 267 (15,600), 319 (9490), 392 (11,250), 466 (4020).Anal. Calcd for C24H19NOS: C, 78.02; H, 5.18; N, 3.79; S, 8.68; O, 4.33. Found: C, 77.95;H, 5.31; N, 3.82; S, 8.54; O, 4.90 (scheme 1).

Reference： [1]Journal of Coordination Chemistry,2015,vol. 68,p. 3685 - 3700

47
[ 90-15-3 ]
[ 68-12-2 ]
[ 574-96-9 ]

Yield	Reaction Conditions	Operation in experiment
82%		General procedure: Solvents such as acetonitrile and dichloroethane were of highest purity HPLC grade.Deionized water was further purified over acid dichromate and alkaline permanganatesolutions before use. All the other chemicals used in this study (organic substrates such ashydrocarbons, phenols, and their substituted compounds) were procured from SigmaAldrich Chemicals (Hyderabad, India) with highest purity (99 %). A carbonate-freesodium hydroxide stock solution was prepared according to standard procedures and theconcentration was systematically checked by titration against potassium hydrogen phthalate.All the metal nitrates used in the present work were of Analytical Reagent (AR) gradeof 99 % purity (S.D. Fine Chemicals Ltd., India). Stock solutions of metal nitrates (Cu(II),Co(II), Ni(II) and Cd(II) nitrates) were prepared in acetonitrile solvent and standardized byEDTA titrations according to literature procedures [33].2.2 VH Reagents Flasks containing DMF dissolved in a suitable solvent {generally dichloroethane (DCE), oracetonitrile (ACN)}, along with SOCl2 and POCl3, were cooled and thermally equilibratedfor about 30 min at -5 C by keeping them in a benzene trough chilled from outside withice and NaCl. Requisite amounts of solvent and amide were transferred into a 100 mL flaskand POCl3 or SOCl2 was added drop wise, at -5 C, with constant stirring. The resultantreagent mixture was kept aside for about an hour to ensure complete formation of the VHadduct. Its concentration was checked by acid-base titration to the bromocresol green endpoint according to literature reports [9-14]. 2.3 Kinetic MethodOrganic substrates such as hydrocarbons, phenols, and their substituted derivatives wereused for kinetic studies of VH reactions in ACN and DCE. The thermostat (Toshniwal,India) was adjusted to the desired reaction temperature (with a precision of ±0.1 C). Twodifferent flasks, one containing known amount of Vilsmeier-Haack reagent (DMF/SOCl2or DMF/POCl3) in a suitable solvent, and the other with the substrate solution, were takenand clamped in the thermostatic bath for about 30 min. The reaction was initiated by adding the requisite amount of substrate solution to the reaction vessel containing the othercontents of the reaction mixture. The entire reaction mixture was stirred until the end of thereaction. A kinetic method was adopted to monitor progress of the VH reaction, which issimilar to that reported in our earlier papers [11-14]. Aliquots of the reaction mixture werewithdrawn into a conical flask, containing considerable (and known) amount of hot distilledwater, at different time intervals. The unreacted VH adduct underwent hydrolysis andgave a mixture of acids (hydrochloric and sulfuric acids for DMF/SOCl2 and hydrochloricand phosphoric acids for DMF/POCl3). The acid content was estimated against standardNaOH solution to the bromocresol green end point. Reproducibility of the results wascrosschecked by conducting kinetic runs three to four times. The results were reproduciblewithin ±3 % error. 2.4 Product Analysis Under Kinetic ConditionsAfter completing the kinetic study of the reaction, excess (remaining part of the reactionmixture) was refluxed further and left aside overnight. The solution was then poured into icecoldwater with vigorous stirring and kept aside for about 2 h. The resultant solution wasneutralized with sodium hydrogen carbonate. The organic phase was extracted with DCE, dried over MgSO4 and the solvent evaporated. Products of the reaction were isolated andfound to be formyl derivatives of the substrates (Scheme 1) as characterized by 1H-NMR andmass spectra with comparison to authentic samples and found to be satisfactory (Table 1).

Reference： [1]Journal of Solution Chemistry,2016,vol. 45,p. 371 - 394

48
[ 574-96-9 ]
[ 74-88-4 ]
[ 50493-10-2 ]

Yield	Reaction Conditions	Operation in experiment
80%		To a stirred solution of 193 mg (1.12 mmol, 1.0 eq) <strong>[574-96-9]1-hydroxy-2-naphthaldehyde</strong> (TCI America) dissolved in 5 mL N,N-dimethylformamide at 0 C. was added 49.0 mg (1.23 mmol, 1.2 eq) sodium hydride. The mixture was stirred at 0 C. for 5 min and 140 muL (2.24 mmol, 2.0 eq) methyl iodide was added. The reaction was heated to 60 C. and stirred for 3 h. The reaction was partitioned between ethyl acetate and water, the organic layer washed with water (1×), brine (2×), and dried (MgSO4). The organic layer was concentrated and the residue purified by flash chromatography with a 0-20% ethyl acetate in hexane gradient to provide 165 mg (80%) of product as a light brown solid. 1H-NMR (400 MHz, CDCl3) delta 10.59 (d, J=0.76 Hz, 1H), 8.23 (d, J=8.16 Hz, 1H), 7.86-7.82 (m, 2H), 7.64-7.54 (m, 3H), 4.12 (s, 3H); 13C-NMR (100 MHz) delta 189.6, 162.6, 138.1, 129.4, 128.4, 127.9, 126.9, 124.9, 124.7, 123.2, 122.7, 65.7; LRMS calculated for C12H10O2 (M+H)+ m/z: 1187.1, measured 187.1.

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 5663 - 5668
[2]Patent: US2016/213780,2016,A1 .Location in patent: Paragraph 0133

49
[ 574-96-9 ]
[ 13057-17-5 ]
[ 73220-21-0 ]

Yield	Reaction Conditions	Operation in experiment
68%		General procedure: To a solution of hydroxy-naphthaldehyde (1 equiv.) in dry DMF(1 mL/mmol)was added, at 0 C, sodium hydride (60% dispersion inmineral oil, 2 equiv.). The reaction mixture was stirred for 15 minthen MOM-Br (2 equiv.) was added and the reaction mixture wasstirred for 1e3 h at rt. The reaction was quenched with brine andextracted 3 times with EtOAc. The organic layer was washed twicewith ice cold brine, dried over MgSO4, filtered and evaporated. Theresidue was purified by flash chromatography on silica gel (cyclohexane/EtOAc 80:20)

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 123,p. 161 - 170

50
[ 109-65-9 ]
[ 574-96-9 ]
1-butoxy-2-naphthaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In acetone;Reflux;	General procedure: The mixture of hydroxy-naphtalene-carboxaldehyde (1 equiv.),K2CO3 (1.5 equiv.) and alkyl halide (1.5 equiv.) in acetone (12 mL/mmol) was stirred under reflux for 4e24 h. When TLC showedcomplete disappearance of the starting materials, solvent wasevaporated under reduced pressure. The residue was purified bycolumn chromatography on silica gel (cyclohexane/EtOAc 90:10 to 70:30)

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 123,p. 161 - 170

51
[ 574-96-9 ]
[ 1198-27-2 ]
1-[(1-hydroxynaphthalen-2-yl)methylidene]amino}naphthalen-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77.6%	In ethanol; at 20℃; for 2h;	Preparation of Compound (1)0.22 g (1.1 mmol) of 1-amino-2-naphthol hydrochloride was dissolved in 2.5 mL of ethanol, and 0.18 g (1 mmol) of <strong>[574-96-9]1-hydroxynaphthalene-2-carbaldehyde</strong> was dissolved in 2.5 mL of ethanol. Were mixed together. The reaction mixture solutionThe mixture was stirred at room temperature for 2 hours until a dark red precipitate was formed. The precipitate is filtered off with cold methanol

Reference： [1]Patent: KR101523284,2015,B1 .Location in patent: Paragraph 0029; 0030; 0031; 0032

52
[ 574-96-9 ]
[ 2009-97-4 ]
ethyl 2-methylnaphtho[1,2-b]furan-3-carboxylate [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 6464 - 6467

53
[ 574-96-9 ]
[ 2009-97-4 ]
ethyl 2-methyl-4-oxo-4H-benzo[h]chromene-3-carboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 9188 - 9195
[2]Journal of Organic Chemistry,2019
[3]Journal of Organic Chemistry,2019,vol. 84,p. 6207 - 6216
[4]Organic Letters,2016,vol. 18,p. 6464 - 6467

54
[ 452-58-4 ]
[ 574-96-9 ]
2,2'-(1E,1'E)-(pyridine-2,3-diylbis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-ylidene)dinaphthalen-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With acetic acid; In methanol;Reflux;	General procedure: To the solution of 2,3-diaminopyridine (1 mmol) and salicylaldehyde (2 mmol) in methanol (20 mL), acetic acid (2-3 drops) was added. The reaction mixture in the ratio 1:2 was stirred and refluxed for about 5-6 h at room temperature (TLC, hexane: ethylacetate, 2:1). The solid product obtained was washed, filtered and recrystallized. A similar procedure was used for the preparation of other Schiff base ligands.

Reference： [1]Asian Journal of Chemistry,2017,vol. 29,p. 669 - 674

55
[ 574-96-9 ]
[ 1761-71-3 ]
C₃₅H₃₈N₂O₂ [ No CAS ]
C₃₅H₃₈N₂O₂ [ No CAS ]

Reference： [1]Journal of Molecular Structure,2018,vol. 1165,p. 305 - 311

56
[ 574-96-9 ]
[ 583-55-1 ]
10-hydroxy-11H-benzo[b]fluoren-11-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With palladium diacetate; potassium hydrogencarbonate; DL-Pro-NHMe; In tert-Amyl alcohol; at 120℃; for 24h;Inert atmosphere;	General procedure: A mixture of arylaldehyde (0.1 g, 1 mmol), dihaloarene (0.565 g, 2 mmol), Pd(OAc)2 (0.022 g, 10.0 mol%), N-phenylpicolinamide (L7, 0.019 g, 15.0 mol%) and potassium hydrogen carbonate (0.5 g, 5 mmol) in tert-amyl alcohol (5.0 ml) was taken in 100.0 ml round bottom flask under N2 atmosphere and stirred for 120C for 24 h. Progress of the reaction was monitored continuously by TLC with ethyl acetate: hexane (2:3) eluent system. After completion of reaction, crude was poured into crushed ice and then filter the reaction mixture. Filtrate then extracted with ethyl acetate (3 times). Organic layer was separated, dried (over anhydrous Na2SO4) and evaporated under reduced pressure and purified by column chromatography to obtain desired product. Characterization data of compounds 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3v and 3x were found exactly similar as reported in the literature (References of above compound are mentioned in Supplementary data).

Reference： [1]Tetrahedron,2019,vol. 75,p. 236 - 245

57
[ 1006-67-3 ]
[ 574-96-9 ]
(Z)-1-hydroxy-N-(3-oxo-3-phenylprop-1-en-1-yl)-2-naphthamide [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 835 - 839

58
[ 574-96-9 ]
[ 98135-75-2 ]
2-(2-(1-hydroxynaphthalen-2-yl)-2-oxoethyl)cyclopentanone [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 1263 - 1267

59
[ 574-96-9 ]
[ 17081-97-9 ]
2-formylnaphthalen-1-yl methyl fumarate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With triethylamine; In dichloromethane; at 0 - 20℃; for 16h;	General procedure: Appropriate benzaldehyde derivative (1 equiv) was dissolved in CH2Cl2 (5 mL·mmol-1) and methyl 3-(chloroformyl)acrylate (2,1.1-2.0 equiv) was added dropwise. The solution was cooled to 0 C and NEt3 (1.6-2.0 equiv) was added dropwise. The resulting suspension was stirred at room temperature for 16 h. The mixture was quenched with H2O (2.5 mL·mmol-1) and washed with saturated aq. KHCO3 solution(2 × 2.5 mL·mmol-1). The organic layer was dried over Na2SO4.Volatiles were removed under vacuum and the crude product was purified by column chromatography on silica gel (cyclohexane:EtOAc).

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 1320 - 1329
[2]Bioorganic and medicinal chemistry,2020

60
[ 5153-67-3 ]
[ 574-96-9 ]
3-nitro-2-phenyl-2H-benzo[h]chromene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1,4-diaza-bicyclo[2.2.2]octane; at 40℃;	General procedure: Substituted salicylaldehydes 1, (1.0 mmol), DABCO (0.2 mmol) and trans-b-nitrostyrenes 2 (1.0 mmol) were taken in one pot and stirred under reflux condition at 40 _C for 1-3 h. The reaction was monitored by TLC and after completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous Na2SO4, and evaporated under reduced pressure. The crude reaction mixture was crystallized by isopropanol. Also in some cases, the crude product was purified by silica gel (100-200 mesh) column chromatography using ethyl acetate/hexane to furnish the pure compound 3 in 74-94% yield. All compounds were characterized by NMR and Mass spectral data.

Reference： [1]Synthetic Communications,2019,vol. 49,p. 1823 - 1835

61
[ 574-96-9 ]
[ 922-67-8 ]
(E)-methyl 3-((2-formylnaphthalen-1-yl)oxy)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With 4-methyl-morpholine; In dichloromethane; at 0 - 20℃; for 20h;	General procedure: To a solution of 2-hydroxybenzaldehyde (s1) (539 mg, 4.41 mmol) in CH2Cl2 (15.2 mL) weresuccessively added methyl propiolate (0.50 mL, 4.55 mmol) and N-methylmorpholine (20 muL, 0.22mmol) at 0 C. After being stirred for 20 h at room temperature, the reaction mixture wereconcentrated in vacuo The residue was purified by column chromatography (silica gel,hexane/EtOAc = 6/1) to give 1a (800 mg, 88%) as white solid.

Reference： [1]Chemistry Letters,2019,vol. 48,p. 337 - 340

62
[ 1603-41-4 ]
[ 574-96-9 ]
C₁₇H₁₄N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	In ethanol; at 60℃; for 5h;	The probe 1 was prepared and purified according to a previous reported method [49]. 2-hydroxy-1-naphthaldehyde (10 mmol, 1.722 g) was added to a solution of 5-methyl-2-amine pyridine (10 mmol, 1.081 g) dissolved in 50mL ethanol. The resultant reaction mixture was heated at 60 C for 5h (Scheme 1). After allowing the evaporation of solvent, the product was washed by cold ethanol to afford orange solid in 83% yield. 1H NMR (CDCl3, 500MHz): delta (ppm) 9.98 (d, 1H), 8.30 (d, 1H), 8.18 (d, 1H), 7.75 (d, 1H), 7.62 (d, 1H), 7.58 (m, 1H), 7.51 (t, 1H), 7.30 (t, 1H), 7.10 (d, 1H), 6.93 (d, 1H), 2.37 (s, 3H). 13C NMR (CDCl3, 500MHz): delta (ppm) 178.09, 150.89, 150.45, 149.21, 139.37, 139.05, 134.27, 131.01, 129.39, 128.56, 127.08, 124.70, 123.86, 119.44, 115.69, 108.72, 18.05.

Reference： [1]Tetrahedron Letters,2019,vol. 60

63
[ 574-96-9 ]
[ 790300-19-5 ]
2-methylene-3,4-dihydro-2H-benzo[h]chromen-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,3-bis-(diphenylphosphino)propane; potassium formate; In 1,4-dioxane; water; at 65℃; for 10h;Inert atmosphere; Sealed tube;	General procedure: To a test tube containing HCO2K (5.0 equiv), 5b-m (1 equiv), Pd2(dba)3·CHCl3 (5mol%), and dppp (15 mol%) in 1,4-dioxane-H2O (4:1, 0.10 M) was added propargylcarbonate 1B (5.0 equiv) under argon. The resulting mixture was sealed with a screwcap and stirred at 65 C for the time shown in Table S4. After being cooled to roomtemperature, the mixture was treated with water. The aqueous layer was extracted withEtOAc twice. The combined organic layers were washed with brine, dried over MgSO4,and concentrated in vacuo. The residue was purified by silica gel chromatography andpreparative TLC to afford 11(b-m)A.

Reference： [1]Chemistry Letters,2019,vol. 48,p. 1402 - 1405

64
[ 574-96-9 ]
[ 30991-44-7 ]
(E)-3,5-di-tert-butyl-2-hydroxy-N'-((1-hydroxynaphthalen-2-yl)methylene)benzohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In methanol; at 20℃; for 3h;	A 3,5-di-tert-butyl-2-hydroxybenzohydrazide was synthesized as reported earlier by our research group [23]. Methanolic solution of 2-Hydroxy-1-naphthaldehyde (1g; 5.8mmol) was mixed with a methanolic solution of 3,5-di-tert-butyl-2-hydroxybenzohydrazide (1.5g; 5.8mmol) and stirred for 3h. Completion of the reaction was monitored by TLC (thin layer chromatography). The resulting precipitate was filtered, washed with methanol and dried in air. Color: yellow, yield: 87 %, m.p: 284-286C, Anal. Calcd for C26H30N2O3 (%): C, 74.61; H, 7.22; N, 6.69. Found (%): C, 73.90; H, 7.19; N, 6.58. IR (cm-1): 3392 (O-H, broad), 3186 (N-H), 1634, (C=O), 1606 (C=N). 1H-NMR (400MHz, DMSO-d6, ppm): 1.35 (9H, s, tert-Bu, C17H, C18H, C19H), 1.40 (9H, s, tert-Bu, C23H, C24H, C25H), 7.48 (1H, d, C20H, J =2Hz), 9.54 (1H, s, C11H), 7.77 (1H, d, C14H, J =2.4Hz), 12.26 (1H, s, N2H), 12.60 (1H, s, O3H), 12.96 (1H, s, O1H), 7.62 (C9H, t, J =7.20Hz), 7.72-8.40 (C3-C8). 13C-NMR (100MHz, DMSO-d6, ppm): 31.31 ((CH3)3), 34.24 ((CH3)3), 29.20 (C-(CH3)3), 34.74 (C-(CH3)3), 118.40 (C10), 158.38 (C11), 167.13 (C12), 136.68 (C21), 128.57 (C20), 139.85 (C15), 121.14 (C14),148.14 (C26) 158.34 (C1), 120-130 (C2-C9). EI-MS: m/z - 418 [M] +.

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2020,vol. 390

65
[ 574-96-9 ]
[ 78-95-5 ]
1-(naphtho[1,2-b]furan-2-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In acetone; for 5h;Reflux;	Weigh compound 19-1 (500 mg, 2.9 mmol) in acetone (30 mL), Then potassium carbonate (522 mg, 3.78 mmol) was sequentially added, 1-chloroacetone (322 muL, 3.5 mmol). The system was reacted at reflux for 5h. After the reaction was completed, ethyl acetate (20 mL) was added to dilute the reaction solution. The solids in the system were filtered by suction filtration, and the filtrate was evaporated to dryness under reduced pressure. The residue was purified by column chromatography (eluent: petroleum ether / ethyl acetate = 20: 1-15: 1), Compound 19-2 (yellow-white solid, 565 mg) was obtained.

Reference： [1]Patent: CN110627817,2019,A .Location in patent: Paragraph 0336-0339

66
[ 574-96-9 ]
[ 937-39-3 ]
N'-((1-hydroxynaphthalen-2-yl)methylene)-2-phenylacetohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In ethanol; for 3h;Reflux;	General procedure: A mixture of 2-phenylacetohydrazide (0.01 mol, 1.5 g) and 20-hydroxy acetophenone (0.01mol, 1.2 ml) was refluxed in absoluteethanol for 3 h at which a yellow product was separated. The residuewas filtered off, washed with cold ethanol for several timesand then recrystallized from hot ethanol to give a crystalline yellowproduct (yield = 80%).

Reference： [1]Journal of Molecular Structure,2020,vol. 1208

67
[ 574-96-9 ]
[ 4848-43-5 ]
2-((2-(diphenylphosphino)ethylimino)methyl)naphthalen-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	In ethanol; at 20℃; for 12h;	General procedure: A common procedure has been used to prepare all the ligands (i.e., L1 -L4 ). Ligands L1 and L2 were synthesized ( Scheme 1 ) using the condensation reaction between 1-naphthaldehyde / 2-naphthaldehyde and <strong>[4848-43-5]2-<strong>[4848-43-5](diphenylphosphino)ethylamine</strong></strong>. Ligands L3 and L4 were synthesized ( Scheme 1 ) using a similar reaction of 2 -<strong>[4848-43-5](diphenylphosphino)ethylamine</strong> with 1 -hydroxy -2 -acetonaphthone / 1 -hydroxy -2 -naphthaldehyde, respectively ( Scheme 1 ). To a stirred solution of 2 -<strong>[4848-43-5](diphenylphosphino)ethylamine</strong> (1.0 mmol) in ethanol (10 mL), an ethanolic solution of 1.0 mmol of corre- sponding carbonyl compound (1 -naphthaldehyde for L1 , 2 -naphthaldehyde for L2 , 1 -hydroxy -2 -acetonaphthone for L3 and 1 -hydroxy -2 -naphthaldehyde for L4 ) was added drop- wise and the mixture was allowed to stir at room temperature for 12 h. The resultant precipitate was filtered and dried under air to obtain the ligand.

Reference： [1]Journal of Molecular Structure,2022,vol. 1253

68
[ 574-96-9 ]
[ 30608-63-0 ]
tert-butyl (S)-(2-hydroxybutyl)((1-hydroxynaphthalen-2-yl)methyl)carbamate [ No CAS ]
(S)-2-(((2-hydroxybutyl)amino)methyl)naphthalen-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; sodium tetrahydridoborate	a.1 Reference Example 24-(a) (1) Prodution of tert-butyl (S)-(2-hydroxybutyl)((1-hydroxynaphthalen-2-yl)methyl)carbamate To a solution of 1-hydroxy-2-naphthoaldehyde (151 mg) in ethanol (3 mL) was added (2S)-1-amino-2-butanol (91 mg) under argon gas flow with stirring at room temperature, and the resulting mixture was stirred at room temperature for 2 hours. Then, sodium borohydride (51 mg) was added thereto with stirring at room temperature, and the resulting mixture was stirred at room temperature for 30 minutes. After the reaction was completed, to the reaction solution was added 2 M hydrochloric acid until the bubbling disappeared, and a 1 M aqueous solution of sodium hydroxide was added thereto to adjust the pH to about 5.5. Then, the resulting mixed solution was subjected to extraction with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give (S)-2-(((2-hydroxybutyl)amino)methyl)naphthalen-1-ol (149 mg) as a brown oil.

Reference： [1]Current Patent Assignee: YUDAI XING PRODUCTION JOINT STOCK AGENCY; UBE INDUSTRIES LIMITED - EP3978073, 2022, A1

69
[ 574-96-9 ]
[ 30608-63-0 ]
(S)-2-(((2-hydroxybutyl)amino)methyl)naphthalen-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
149 mg	Stage #1: 1-monohydroxy-2-naphthaldehyde; (S)-(+)-1-amino-2-butanol In ethanol at 20℃; for 2h; Inert atmosphere; Stage #2: With sodium tetrahydridoborate In ethanol at 20℃; for 0.5h;	24-(a).1 Prodution of tert-butyl (S)-(2-hydroxybutyl)((1-hydroxynaphthalen-2-yl)methyl)carbamate To a solution of 1-hydroxy-2-naphthoaldehyde (151 mg) in ethanol (3 mL) was added (2S)-1-amino-2-butanol (91 mg) under argon gas flow with stirring at room temperature, and the resulting mixture was stirred at room temperature for 2 hours. Then, sodium borohydride (51 mg) was added thereto with stirring at room temperature, and the resulting mixture was stirred at room temperature for 30 minutes. After the reaction was completed, to the reaction solution was added 2 M hydrochloric acid until the bubbling disappeared, and a 1 M aqueous solution of sodium hydroxide was added thereto to adjust the pH to about 5.5. Then, the resulting mixed solution was subjected to extraction with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give (S)-2-(((2-hydroxybutyl)amino)methyl)naphthalen-1-ol (149 mg) as a brown oil.

Reference： [1]Current Patent Assignee: YUDAI XING PRODUCTION JOINT STOCK AGENCY; UBE INDUSTRIES LIMITED - EP3978073, 2022, A1 Location in patent: Paragraph 1236

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