[ CAS No. 612-19-1 ] {[proInfo.proName]}

Name: 612-19-1|2-Ethylbenzoic acid|98%
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Quality Control of [ 612-19-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 612-19-1 ]

Product Details of [ 612-19-1 ]

CAS No. :	612-19-1	MDL No. :	MFCD00045838
Formula :	C₉H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CGMMPMYKMDITEA-UHFFFAOYSA-N
M.W :	150.17	Pubchem ID :	34170
Synonyms :

Calculated chemistry of [ 612-19-1 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.17
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) :	-5.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.6
Log Po/w (XLOGP3) :	1.82
Log Po/w (WLOGP) :	1.95
Log Po/w (MLOGP) :	2.25
Log Po/w (SILICOS-IT) :	2.01
Consensus Log Po/w :	1.93

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.19
Solubility :	0.971 mg/ml ; 0.00647 mol/l
Class :	Soluble
Log S (Ali) :	-2.22
Solubility :	0.898 mg/ml ; 0.00598 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.54
Solubility :	0.429 mg/ml ; 0.00286 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 612-19-1 ]

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 [ 612-19-1 ]

* 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 [ 612-19-1 ]
Downstream synthetic route of [ 612-19-1 ]

[ 612-19-1 ] Synthesis Path-Upstream 1~2

1
[ 612-19-1 ]
[ 767-90-8 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1918, vol. 417, p. 75
[2] Journal of the American Chemical Society, 1991, vol. 113, # 25, p. 9630 - 9639
[3] Patent: EP3196191, 2017, A1, . Location in patent: Paragraph 0053; 0054

2
[ 496-11-7 ]
[ 22927-13-5 ]
[ 767-90-8 ]
[ 83-33-0 ]
[ 612-19-1 ]

Reference： [1] Chemical Communications (Cambridge, United Kingdom), 2018, vol. 54, # 86, p. 12194 - 12197

[ 612-19-1 ] Synthesis Path-Downstream 1~56

1
[ 577-56-0 ]
[ 612-19-1 ]

Reference： [1]Chemische Berichte,1877,vol. 10,p. 2209
[2]Justus Liebigs Annalen der Chemie,1961,vol. 641,p. 51 - 62
[3]Acta Chemica Scandinavica,1989,vol. 43,p. 381 - 385
[4]Chemische Berichte,1896,vol. 29,p. 2534

2
[ 34136-59-9 ]
[ 612-19-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In ethylene glycol; at 170℃; for 7h;	2-Ethylbenzonitrile (7.6mmol) and KOH (24.8mmol) were suspended in ethane-1,2-diol (10mL) and stirred at 170C for 7h. Then, the reaction mixture was cooled down to rt, H2O (50mL) was added and the resulting mixture was extracted three times with ether (30mL). pH of the aqueous layer was adjusted to 1 by diluted HCl and the aqueous phase was extracted three times with ether (40mL). Organic phases were collected, extracted three times with H2O (40mL) and dried over Na2SO4. The solvent was removed and obtained compound was directly used in the next step. Yield: 89.0%, white solid; mp: 64-65C; IR: 3400-2300 (b, OH), 2977 (as CH3), 2955 (as CH2), 2869 (s CH3), 1681 ( CO), 1601, 1575, 1488, 1447 ( CC aromatic) cm-1; 1H NMR (DMSO-d6, 300MHz): delta 12.79 (1H, br s, COOH), 7.76 (1H, d, J=7.0Hz), 7.43 (1H, t, J=7.5Hz), 7.33-7.21 (2H, m), 2.90 (2H, q, J=7.4Hz, CH2), 1.14 (3H, t, J=7.4Hz, CH3); 13C NMR (DMSO-d6, 75MHz): delta 169.14, 145.12, 131.96, 130.54, 130.35, 130.34, 126.04, 27.03, 16.32.

Reference： [1]Monatshefte fur Chemie,1999,vol. 130,p. 313 - 326
[2]Journal of the Chemical Society,1959,p. 2024,2026
[3]Archiv der Pharmazie,1962,vol. 295 /67,p. 833 - 846
[4]Tetrahedron,2016,vol. 72,p. 2072 - 2083

3
[ 612-19-1 ]
[ 767-90-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	With diborane; In tetrahydrofuran; at 0 - 20℃; for 24h;	A solution of compound 28 (70.0 g, 466 mmol) in dry THF (500 mL) was treated with 10 M solution of BH3in THF (53 mL, 53.0 mmol of BH3) at 0C. The reaction mass was stirred at r.t. for 24h before methanol (150 mL) was slowly added thereto. The resulting mixture was stirred for 45 min, and evaporated under reduced pressure to yield 55.0 g (404 mmol, 87%) of compound 29, pure enough for the next step.
87%	With diborane; In tetrahydrofuran; methanol; at 0 - 20℃; for 24h;	A solution of compound 28 (70.0 g, 466 mmol) in dry THF (500 mL) was treated with 10 M solution of BH3 in THF (53 mL, 53.0 mmol of BH3) at 0C. The reaction mass was stirred at r.t. for 24h before methanol (150 mL) was slowly added thereto. The resulting mixture was stirred for 45 mm, and evaporated under reduced pressure to yield 55.0 g (404 mmol, 87%) ofcompound 29, pure enough for the next step.
	With borane-THF; In tetrahydrofuran; at 20℃; for 3h;Cooling with ice;	0.30 g (2 mmol, 1.0 eq) 38 2-ethyl-benzoic acid (compound 12a) was dissolved in 16 ml anhydrous 39 THF, then 4 ml (4 mmol, 2.0 eq) 1M 40 BH3/THF solution was added dropwise under the condition of ice bath. After reacting at room temperature for 3.0 hours, THF was removed by vacuum distillation. 1 M HCl (41 aq) was added in the reaction system under the condition of ice water bath until no more air bubble came out. Then water and EA(10 ml*2) were added for extract and the organic phase was washed twice with saturated sodium bicarbonate solution and then twice with saturated sodium chloride solution.The solution was dried over anhydrous sodium sulfate and desolventlized to gain light yellow oily material (Compound 13g). The crude product was used without purification in the next step directly. 42 Benzyl alcohol intermediate compound 13h to 13m can be obtained with the same reduction method from compound 12b to 12g.

With diborane; In tetrahydrofuran; at 0 - 20℃; for 3h;

General procedure: To a solution of benzoic acids 16a-16e (2 mmol) in anhydrous THF (16 ml) was added the solution of BH3 in THF (4 ml, 4 mmol) slowly at 0 C. The reaction mixture was stirred at room temperature for 3.0 h. After the organic solvent was evaporated, the residual was extracted by ethyl acetate. The extract was washed with NaHCO3 (aq), brine and dried over Na2SO4. The organic layer was condensed and the crude product was obtained as light yellow oils. The 17e-17i were used directly for the next step without further purification. (2-ethylphenyl)methanol 17e, yield 80.4%, ESI-MS(m/z): 137.1[M+H]+.

Reference： [1]Patent: WO2019/86142,2019,A1 .Location in patent: Page/Page column 76
[2]Patent: WO2019/86141,2019,A1 .Location in patent: Page/Page column 105
[3]Justus Liebigs Annalen der Chemie,1918,vol. 417,p. 75
[4]Journal of the American Chemical Society,1991,vol. 113,p. 9630 - 9639
[5]Patent: EP3196191,2017,A1 .Location in patent: Paragraph 0053; 0054
[6]European Journal of Medicinal Chemistry,2019,vol. 163,p. 864 - 882

4
[ 612-19-1 ]
[ 76118-05-3 ]

Reference： [1]Journal of Organic Chemistry,1939,vol. 4,p. 1,9
[2]Chemische Berichte,1896,vol. 29,p. 2534
[3]Recueil des Travaux Chimiques des Pays-Bas,1962,vol. 81,p. 93 - 101
[4]Journal of Medicinal Chemistry,1982,vol. 25,p. 145 - 152
[5]Journal of Medicinal Chemistry,1983,vol. 26,p. 1187 - 1192
[6]Monatshefte fur Chemie,1999,vol. 130,p. 313 - 326
[7]Pesticide Science,1994,vol. 41,p. 139 - 148
[8]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3057 - 3068
[9]Journal of Medicinal Chemistry,2006,vol. 49,p. 2232 - 2240
[10]Journal of Medicinal Chemistry,2010,vol. 53,p. 2601 - 2611
[11]Angewandte Chemie - International Edition,2013,vol. 52,p. 2194 - 2197
Angew. Chem.,2013,vol. 125,p. 2250 - 2253,4
[12]Chemical Communications,2015,vol. 51,p. 1371 - 1374
[13]Journal of the American Chemical Society,2015,vol. 137,p. 7564 - 7567
[14]Tetrahedron,2016,vol. 72,p. 2072 - 2083
[15]Journal of the American Chemical Society,2016,vol. 138,p. 12771 - 12774
[16]Organic and Biomolecular Chemistry,2019,vol. 17,p. 8768 - 8777
[17]Journal of Organic Chemistry,2020

5
[ 612-19-1 ]
[ 439937-55-0 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 7631 - 7639
[2]Archiv der Pharmazie,1962,vol. 295 /67,p. 833 - 846

6
[ 118-90-1 ]
[ 74-88-4 ]
[ 612-19-1 ]

Reference： [1]Monatshefte fur Chemie,1999,vol. 130,p. 313 - 326
[2]Journal of the American Chemical Society,1991,vol. 113,p. 4931 - 4936
[3]Synthetic Communications,1986,vol. 16,p. 575 - 584
[4]Tetrahedron Asymmetry,1997,vol. 8,p. 3765 - 3774
[5]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 1077 - 1081

7
[ 67-56-1 ]
[ 612-19-1 ]
[ 50604-01-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sulfuric acid;Reflux;Product distribution / selectivity;	a) 2-Ethyl-benzoic acid methyl ester; [0172] 2-Ethyl-benzoic acid (3.0 g, 17.6 mmol) was dissolved in MeOH (20 mL) and sulfuric acid (1 mL) was added. The mixture was refluxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated Na2CO3 to basic pH. The organic phase was dried and evaporated under reduced pressure, and the product (3.1 g, yield 96%) was used without further purificationC9H9ClO2 1H-NMR (dmso-de): 2.48 (3H, br s); 3.82 (3H, s); 7.31 (1H, t, J=7.6 Hz); 7.63-7.67 (2H, m).
88 - 96%	sulfuric acid;Heating / reflux;Product distribution / selectivity;	a) 2-Ethyl-ben?oic acid methyl ester2-Ethyl-benzoic acid (3.0 g, 17.6 mmol) was dissolved in MeOH (20 mL) and sulfuric acid (ImL) was added. The mixture was refluxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated Na2CO3 to basic pH. The organic phase was dried and evaporated under reduced pressure, and the product (3.1 g5 yield 96%) was used without further purification.C9H9C1O21H-NMR (dmso-d6): 2.48 (3H5 br s); 3.82 (3H, s); 7.31 (IH5 t, J=7.6 Hz); 7.63-7.67 (2H5 m). ; a) 2-Ethyl-benzoic acid methyl ester2-Ethyl-benzoic acid (3.0 g, 20.0 mmol) was dissolved in MeOH (20 mL) and catalytic quantity of sulfuric acid (ImL) was added. The mixture was refluxed overnight, after that the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated Na2CO3 to basic pH. The organic phase was dried and evaporated under reduced pressure, and the product (2.9 g, yield 88%) was used without further purificationC10H12O21H-NMR (dmso-d6): 1.12 (3H, t, J=7.2 Hz); 2.86 (2H, q, J=7.2 Hz); 3.81 (3H,
88 - 96%	sulfuric acid;Heating / reflux;Product distribution / selectivity;	2-Ethyl-benzoic acid (3.0 g, 17.6 mmol) was dissolved in MeOH (20 mL) and sulfuric acid (1 mL) was added. The mixture was refiuxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated Na2CO3 to basic pH. The organic phase was dried and evaporated <n="48"/>under reduced pressure, and the product (3.1 g, yield 96%) was used without further purificationC9H9ClO21H-NMR (dmso-d6): 2.48 (3H, br s); 3.82 (3H, s); 7.31 (IH, t, J=7.6 Hz); 7.63-7.67 (2H, m).; 2-Ethyl-benzoic acid (3.0 g, 20.0 mmol) was dissolved in MeOH (20 mL) and catalytic quantity of sulfuric acid (1 mL) was added. The mixture was refluxed overnight, after that the solvent was evaporated under reduced pressure; the crude was <n="49"/>dissolved in DCM and washed with saturated Na2CO3 to basic pH. The organic phase was dried and evaporated under reduced pressure, and the product (2.9 g, yield 88%) was used without further purification1H-NMR (dmso-d6): 1.12 (3H, t, J=7.2 Hz); 2.86 (2H, q, J=7.2 Hz); 3.81 (3H, s); 7.27-7.34 (2H, m); 7.46-7.51 (IH, m); 7.73-7.75 (IH, m).

With sulfuric acid;

General procedure: Compound 1a was purchased from Fluka and was used without further purification. The remaining compounds 1b-m were prepared from the corresponding acetophenones (or benzoate esters) 10b-m as described below. Compound 1f was prepared both from 2-nitroacetophenone (as described in Scheme 1) and by reaction of 2-ethyl-nitrobenzene and paraformaldehyde.15 The latter procedure was employed in the following experimental section. Acetophenones 10c, 10d, 10j, and 10k are commercially available. Acetophenones 10b, 10l, and 10m are known compounds and were prepared as previously described.13b Acetophenone 10i was prepared by methylation of 2,6-dihydroxy-4-methylacetophenone16 K. Tsujihara, M. Hongu, K. Saito, H. Kawanishi, K. Kuriyama, M. Matsumoto, A. Oku, K. Ueta, M. Tsuda and A. Saito, J. Med. Chem. 42 (1999), pp. 5311-5324. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (55)16 with Me2SO4 and Na2CO3 in refluxing acetone. Methyl esters 10e, 10g, and 10h were prepared by esterification (MeOH/H2SO4) of the corresponding benzoic acids. 2-Iodo-benzoic acid and 2-methyl-benzoic acid are commercially available. 2-Ethyl-benzoic acid was obtained by the reaction of an ether solution of (2-ethylphenyl)-magnesium iodide with carbon dioxide. The latter Grignard reagent was prepared starting from 2-ethyl-iodobenzene which was obtained from 2-ethyl-aniline.17

Reference： [1]Patent: WO2010/9290,2010,A1 .Location in patent: Page/Page column 63-64
[2]Patent: WO2008/87529,2008,A1 .Location in patent: Page/Page column 47; 48
[3]Patent: WO2009/91832,2009,A1 .Location in patent: Page/Page column 46-47; 47-48
[4]Journal of Organic Chemistry,1979,vol. 44,p. 1519 - 1533
[5]Tetrahedron Asymmetry,2011,vol. 22,p. 619 - 628

8
[ 612-19-1 ]
[ 3453-64-3 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 3129 - 3132
[2]Synlett,2010,p. 2325 - 2329
[3]Journal of the Chemical Society. Perkin transactions I,1999,p. 1713 - 1716
[4]Tetrahedron Letters,2001,vol. 42,p. 1647 - 1649
[5]Arzneimittel-Forschung/Drug Research,2005,vol. 55,p. 588 - 597
[6]Tetrahedron Letters,1995,vol. 36,p. 7089 - 7092
[7]Journal of the Chemical Society. Perkin transactions I,1997,p. 787 - 793
[8]Synthetic Communications,2003,vol. 33,p. 3435 - 3453

9
[ 612-19-1 ]
[ 3413-14-7 ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 3765 - 3774

10
[ 124-38-9 ]
(2-ethylphenyl)magnesium iodide [ No CAS ]
[ 612-19-1 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether;	Compound 1a was purchased from Fluka and was used without further purification. The remaining compounds 1b-m were prepared from the corresponding acetophenones (or benzoate esters) 10b-m as described below. Compound 1f was prepared both from 2-nitroacetophenone (as described in Scheme 1) and by reaction of 2-ethyl-nitrobenzene and paraformaldehyde.15 The latter procedure was employed in the following experimental section. Acetophenones 10c, 10d, 10j, and 10k are commercially available. Acetophenones 10b, 10l, and 10m are known compounds and were prepared as previously described.13b Acetophenone 10i was prepared by methylation of 2,6-dihydroxy-4-methylacetophenone16 with Me2SO4 and Na2CO3 in refluxing acetone. Methyl esters 10e, 10g, and 10h were prepared by esterification (MeOH/H2SO4) of the corresponding benzoic acids. 2-Iodo-benzoic acid and 2-methyl-benzoic acid are commercially available. 2-Ethyl-benzoic acid was obtained by the reaction of an ether solution of (2-ethylphenyl)-magnesium iodide with carbon dioxide. The latter Grignard reagent was prepared starting from 2-ethyl-iodobenzene which was obtained from 2-ethyl-aniline.17 F. Weygand, H. Weber, E. Maekawa and G. Eberhardt, Chem. Ber. 89 (1956), pp. 1994-1999. Full Text via CrossRef17

Reference： [1]Monatshefte fur Chemie,1999,vol. 130,p. 313 - 326
[2]Tetrahedron Asymmetry,2011,vol. 22,p. 619 - 628

11
[ 7664-93-9 ]
[ 612-19-1 ]
lead-cathode [ No CAS ]
[ 767-90-8 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1918,vol. 417,p. 75

12
[ 612-19-1 ]
[ 4702-34-5 ]
[ 3453-64-3 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 1375 - 1379

13
[ 16254-21-0 ]
[ 612-19-1 ]
1-(4-chlorophenyl)-3-dimethylaminopropyl 2-ethylbenzoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 2232 - 2240

14
[ 612-19-1 ]
[ 59635-98-2 ]

Yield	Reaction Conditions	Operation in experiment
72%		<strong>[612-19-1]2-<strong>[612-19-1]ethylbenzoic acid</strong></strong> (1.0 g, 6.66 mmol) in methanol (30 ml) of concentrated hydrochloric acid (202 mul, 6.66 mmol) at room temperature was added dropwise. After the atmosphere was replaced with argon, and the mixture was heated and stirred under reflux conditions overnight. After was concentrated to dryness under reduced pressure, was dissolved in ethanol (1 ml), was added hydrazine monohydrate (969 mul, 19.98mmol). Under microwave irradiation, and the mixture was stirred for 2 hours at 100 . Furthermore hydrazine monohydrate (969 mul, 19.98 mmol) was added, under microwave irradiation, and the mixture was stirred for 2 hours at 100 . After it was concentrated to dryness under reduced pressure, saturated brine, saturated aqueous sodium hydrogen carbonate solution was added, followed by extraction with chloroform. Dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. To give the title compound (783 mg, 72%).

Reference： [1]Patent: JP2016/124812,2016,A .Location in patent: Paragraph 0286
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 1187 - 1192
[3]Journal of Medicinal Chemistry,1983,vol. 26,p. 1187 - 1192

15
[ 612-19-1 ]
[ 74533-20-3 ]

Reference： [1]Journal of the American Chemical Society,1991,vol. 113,p. 9630 - 9639
[2]Recueil des Travaux Chimiques des Pays-Bas,1960,vol. 79,p. 1211 - 1222

16
[ 612-19-1 ]
[ 1467-06-7 ]

Reference： [1]Journal of the American Chemical Society,1991,vol. 113,p. 9630 - 9639
[2]Recueil des Travaux Chimiques des Pays-Bas,1960,vol. 79,p. 1211 - 1222

17
[ 612-19-1 ]
[ 22927-13-5 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1918,vol. 417,p. 75
[2]Patent: WO2019/86142,2019,A1
[3]Patent: WO2019/86141,2019,A1

18
[ 612-19-1 ]
[ 2486-74-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: concentrated nitric acid / Behandeln mit konz. Schwefelsaeure mit Trennung des Gemisches durch fraktionierte Krystallisation aus Wasser, Chloroform oder Benzol 2: tin; hydrochloric acid

Reference： [1]Giebe [Chemische Berichte, 1896, vol. 29, p. 2534]

19
[ 28290-06-4 ]
[ 105-53-3 ]
[ 612-19-1 ]
[ 129075-82-7 ]

Yield	Reaction Conditions	Operation in experiment
3.5 g (27%)	With thionyl chloride; NaH; hydrogen;Pd-C; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol; hexane; N,N-dimethyl-formamide; toluene;	2-Ethylphenylmethyl propanedioic acid, diethyl ester A mixture of 19.7 g (131 mmol) of <strong>[612-19-1]2-<strong>[612-19-1]ethylbenzoic acid</strong></strong> and 100 ml of thionyl chloride was heated under reflux for five hours. The reaction was concentrated, 50 ml of toluene was added, and the mixture was concentrated again to remove the last traces of thionyl chloride (done three times). The resulting dark liquid was dissolved in 50 ml of DMF and added dropwise over 20 minutes at 0 to a solution of sodium diethyl malonate in 250 ml of DMF [prepared by adding 23.0 g (143 mmol) of diethyl malonate in 100 ml of DMF to a suspension of 5.8 g (145 mmol) of NaH (60% oil dispersion) which had been washed with n-hexane and suspended in 150 ml of DMF]. The mixture was allowed to warm to room temperature over two hours and then was poured into 500 ml of ice water and extracted with ether. The ether extracts were washed with saturated sodium chloride, dried (MgSO4), and concentrated. The residue was chromatographed (SiO2, n-hexane to 9:1 n-hexane/ether) to give 16.5 g (45%) of a colorless oil suitable for use in the next step. A mixture of 13.4 g (45.9 mmol) of the ketone in 100 ml of ethanol and 2.0 g of 20% Pd-C was hydrogenated at room temperature until two equivalents of hydrogen were taken up. The mixture was filtered and concentrated. The residue was chromatographed (SiO2, hexane to 9:1 hexane/ether) to give 3.5 g (27%) of 2-ethylphenylmethyl propanedioic acid, diethyl ester as a colorless oil.

Reference： [1]Patent: US5177075,1993,A

20
[ 144-55-8 ]
[ 612-19-1 ]
[ 50604-01-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sulfuric acid; In methanol;	EXAMPLE 24 2,3-Dimethylphthalimidine A solution of 11.8 g. (0.076 mole) of <strong>[612-19-1]2-<strong>[612-19-1]ethylbenzoic acid</strong></strong> in 25 ml. of absolute methanol is treated cautiously with 2.5 ml. of concentrated sulfuric acid and heated to reflux. After 4 hours, the mixture is poured onto ice and the oily product is extracted into ether. Evaporation of the washed (water, 5% aqueous sodium bicarbonate and water) and dried extract under reduced pressure leaves methyl 2-ethylbenzoate as the residual colorless oil in a yield of 86%.

Reference： [1]Patent: US4064139,1977,A

21
[ 97-94-9 ]
[ 88-67-5 ]
[ 612-19-1 ]

Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 415 - 422

22
[ 1093987-89-3 ]
[ 612-19-1 ]
[ 1093989-01-5 ]

Yield	Reaction Conditions	Operation in experiment
		THF (5 ml_), 2-{4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}acetohydrazide (50.0 mg, 0.141 mmol), <strong>[612-19-1]2-<strong>[612-19-1]ethylbenzoic acid</strong></strong> (21.2 mg, 0.141 mmol), HATU (53.6 mg, 0.141 mmol,) and DIPEA (0.049 ml_, 0.282 mmol) were combined and the reaction mixture was stirred at room temperature for 45 minutes. Methoxycarbonyl sulfamoyltriethylammonium hydroxide inner salt (130 mg, 0.565 mmol) was added and the reaction was stirred overnight. The reaction mixture was diluted with ethyl acetate and washed with water. The solvent was removed and the crude material was purified via silica gel chromatography to give 37 mg of the title compound. 1 H NMR (400 MHz, CHLOROFORM-tf) delta ppm 7.80 (d, 1 H), 7.38 - 7.48 (m, 1 H), 7.25 - 7.37 (m, 5 H), 7.13 (s, 1 H), 7.01 (s, 1 H), 4.33 (s, 2 H), 3.03 (q, 2 H), 1.19 (t, 3 H).

Reference： [1]Patent: WO2008/157330,2008,A1 .Location in patent: Page/Page column 106

23
(2S,2'S)-N,N'-(4,4'-((E)-ethene-1,2-diyl)bis(4,1-phenylene))dipyrrolidine-2-carboxamide dihydrochloride [ No CAS ]
[ 612-19-1 ]
[ 916446-61-2 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1976 - 1994

24
[ 612-19-1 ]
[ 1261658-58-5 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1514 - 1517

25
[ 612-19-1 ]
[ 892390-46-4 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 5955 - 5958
Angew. Chem.,2014,vol. 126,p. 6065 - 6068,4

26
[ 504-29-0 ]
[ 612-19-1 ]
2-ethyl-N-(pyridin-2-yl)benzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 6393 - 6402

27
4-amino-N-(4-methoxycyclohexyl)-1H-pyrazole-3-carboxamide [ No CAS ]
[ 612-19-1 ]
4-(2-ethylbenzamido)-N-(4-methoxycyclohexyl)-1H-pyrazole-3-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 7536 - 7549

28
[ 612-19-1 ]
2-ethyl-5-iodobenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium periodate; sulfuric acid; iodine; acetic anhydride; acetic acid; at 5 - 20℃; for 19h;	2-ethyl-5-iodobenzoic acidNalO4 (5.56 g, 26.0 mmol) and I2 (4.31 g, 17.00 mmol) was ground together then was added AcOH (37.2 mL, 650 mmol) and Ac20 (18.87 mL, 200 mmol). To this mixture was then slowly added H2S04(cone.) (18.66 mL, 350 mmol) in ice-water bath to keep temperature below 5 C while adding. To the above reaction mixture was added 2- <strong>[612-19-1]ethylbenzoic acid</strong> (7.51 g, 50 mmol) (ground). The resulting reaction mixture was stirred at RT for 19 h. The reaction mixture was poured into ice-water (150/150 g) and stirred at RT for 30 min before was filtered, washed with H20 (2 x 30 mL), to afford 2-ethyl-5- iodobenzoic acid (14.7552 g, 53.4 mmol, 107 % yield). LC-MS m/z 277 (M + H)+, 0.95 (ret. time).

Reference： [1]Patent: WO2015/92713,2015,A1 .Location in patent: Page/Page column 132; 1

29
[ 501-65-5 ]
[ 612-19-1 ]
(E)-(1-(3-ethylphenyl)ethene-1,2-diyl)dibenzene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 6933 - 6937
Angew. Chem.,2016,vol. 128,p. 7047 - 7051,5

30
4-hydroxybutyl 2-chloroacetate [ No CAS ]
[ 612-19-1 ]
2-(4-hydroxybutoxy)-2-oxoethyl 2-ethylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With triethylamine; In acetone; at 50℃; for 5h;	Et3N (365 mg, 3.61 mmol) and 4-hydroxybutyl 2-chioroacetate (300 mg, 1.81 mmol) was added to a stirred solution of <strong>[612-19-1]2-<strong>[612-19-1]ethylbenzoic acid</strong></strong> (542 mg, 3.61 mmol) in acetone (10 mL). The reaction was stirred at 50 C for 5 h. After that, the reaction mixture was partitioned between DCM (20 mL) and H20 (10 mL). The aqueous phase was separated and extracted with DCM (10 mL). The combined organic phase was washed with saturated brine (20 mL), dried over anhydrous Na2SO4 and evaporated. The residue was purified by a silica gel flash column with Hex/EA = 6:1 to yield the titled compound (175 mg, 35%) as a colorless oil. ?H NMR was performed at 400MHz with CDC13 as solvent to characterize the titled compound, results are as follows: = 8.02 - 7.95 (m, 1 H), 7.49 - 7.44 (m, 1 H), 7.32 - 7.24 (m, 2 H), 4.83 (s, 2 H), 4.25 (t, J 6.4 Hz, 2 H), 3.67 (t, J= 6.4 Hz, 2 H), 3.08-2.97 (m, 2H), 1.81- 1.74(m,2H), 1.67- 1.60(m,2H), 1.28- 1.22(m,3H).

Reference： [1]Patent: WO2017/49470,2017,A1 .Location in patent: Paragraph 00340; 00341

31
[ 110-63-4 ]
[ 612-19-1 ]
4-hydroxybutyl 2-ethylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 25℃; for 3h;	2,6-dim<strong>[612-19-1]ethylbenzoic acid</strong> (500 mg, 3.33 mmol), DCC (755 mg, 3.67 mmol) and DMAP (50 mg) was added to a stirred solution of butane-1,4-diol (600 mg, 6.67 mmol) in DCM (30 mL). The reaction was stirred at 25 C for 3 h. After that, the reaction mixture was diluted with saturated aqueous NH4C1 (10 mL) and stirred for 5 mm. The aqueous phase was separated and extracted with DCM (10 mL). The combined organic phase was washed with saturated brine (15 mL), dried over anhydrous Na2SO4 and evaporated. The residue was purified by a silica gel flash column with Hex/EA = 8:1 to yield the titled compound (480 mg, 65%) as a colorless oil. ?H NMR was performed at 400IVIHz with CDC13 as solvent to characterize the titled compound, results are as follows: = 7.84 (d, J = 8.0 Hz, 1 H), 7.43 (t, J = 7.4 Hz, 1 H), 7.28 - 7.22 (m, 2 H), 4.34 (t, J = 6.6 Hz, 2 H), 3.73 (t, J = 6.0 Hz, 2 H), 2.98 (q, J= 7.6Hz, 2H), 1.91- 1.84(m, 2H), 1.77- 1.70(m, 2H), 1.24(t, J=7.4 Hz, 3 H).

Reference： [1]Patent: WO2017/49470,2017,A1 .Location in patent: Paragraph 00283; 00284

32
[ 710328-02-2 ]
[ 612-19-1 ]
2-ethyl-N-(2-(4-ethylpiperazin-1-yl)-4-methylquinolin-6-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22.1%		General procedure: Aromatic carboxylic acid (1.11mmol), EDCI (213mg, 1.11mmol), HOBt (150mg, 1.11mmol) were added into 10ml DCM. The mixture was stirred at rt for 1h. Then Et3N (0.31ml, 2.22mmol) and intermediate 17 (200mg, 0.74mmol) were added. After stirring at rt for 24h, the reaction was washed with 2mol/L NaOH solution (20ml×3) and saturated NH4Cl solution (20ml×1), dried over anhydrous Na2SO4 and then concentrated. The residue was purified by normal phase column chromatography to afford the desired compound.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 141,p. 1 - 14

33
[ 1663-39-4 ]
[ 612-19-1 ]
(E)-tert-butyl-2-(4-ethyl-3-oxoisobenzofuran-1(3H)-ylidene)acetate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 3520 - 3525

34
[ 934405-30-8 ]
[ 612-19-1 ]
N-(4-chloro-2-(2-(2-ethylbenzoyl)hydrazinecarbonyl)-6-methylphenyl)-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; O?(1H?benzotriazol?1?yl)?N,N,N?,N??tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; at 20℃; for 3h;Green chemistry;	The intermediate N- (4-chloro-2- (formylhydrazino) -6-methylphenyl) -3-bromo- 1 - (3-chloropyridin-2-yl) Pyrazole-5-carboxamide (1.00 g, 2.07 mmol) and<strong>[612-19-1]2-Ethylbenzoic acid</strong> (0.31 g, 2.07 mmol)Was dissolved in N, N-dimethylformamide (DMF) followed by the coupling reagent O-benzotriazole-N, N, N ', N'- tetramethyluronium tetrafluoroborate (TBTU )(0.66 g, 2.07 mmol). N, N-diisopropylethylamine (DIPEA) (0.80 g, 6.20 mmol) was added dropwise and the mixture was stirred at ambient temperature for 3 h.TLC point plate tracking, the point of disappearance of raw materials, the reaction solution into 500mL saturated salt water, stirred 0.5h, fully precipitated, filtered to give the crude product, dried and purified by column chromatography.

Reference： [1]Patent: CN107011335,2017,A .Location in patent: Paragraph 0101;. 0102

35
[ 1233882-37-5 ]
[ 612-19-1 ]
N-(4-bromo-2-(2-(2-ethylbenzoyl)hydrazinecarbonyl)-6-methylphenyl)-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; O?(1H?benzotriazol?1?yl)?N,N,N?,N??tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; at 20℃; for 3h;Green chemistry;	The intermediate N- (4-bromo-2- (formylhydrazino) -6-methylphenyl) -3- bromo-l- (3- chloropyridin- 2-yl) -lH- Pyrazole-5-carboxamide (1.00 g, 1.89 mmol) and<strong>[612-19-1]2-<strong>[612-19-1]ethylbenzoic acid</strong></strong>(0.28 g, 1.89 mmol) was dissolved in N, N-dimethylformamide (DMF) followed by the coupling reagent O-benzotriazole-N, N, N ', N'-tetramethylurea Tetrafluoroborate (TBTU)(0.60 g, 1.89 mmol). N, N-diisopropylethylamine (DIPEA) (0.73 g, 5.68 mmol) was added dropwise and the mixture was stirred at ambient temperature for 3 h.TLC point plate tracking, the point of disappearance of raw materials, the reaction solution into 500mL saturated salt water, stirred 0.5h, fully precipitated, filtered to give the crude product, dried and purified by column chromatography.

Reference： [1]Patent: CN107011335,2017,A .Location in patent: Paragraph 0103; 0104

36
[ 1629-58-9 ]
[ 612-19-1 ]
2-ethyl-6-(3-oxopentyl)benzoic acid [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 1358 - 1363

37
[ 524-38-9 ]
[ 612-19-1 ]
1,3-dioxoisoindolin-2-yl 2-ethylbenzoate [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 3296 - 3299

38
[ 85342-65-0 ]
[ 612-19-1 ]
4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl 2-ethylbenzoate [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 3296 - 3299

39
2-hydroxy-1H-benzo[f]isoindole-1,3(2H)-dione [ No CAS ]
[ 612-19-1 ]
1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl 2-ethylbenzoate [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 3296 - 3299

40
[ 5666-17-1 ]
[ 612-19-1 ]
2-allyl-6-ethylbenzoic acid [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 4337 - 4340

41
[ 7499-07-2 ]
[ 612-19-1 ]
[ 54109-03-4 ]
[ 13049-38-2 ]
3,3'-dichloro-5,5'-dimethyl-1,1'-biphenyl [ No CAS ]
3-chloro-3'-ethyl-5-methyl-1,1'-biphenyl [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2644 - 2649

42
[ 612-19-1 ]
[ 13049-38-2 ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2644 - 2649

43
[ 612-19-1 ]
3-bromo-2-ethyl-5-nitrobenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1 3-Bromo-2-ethyl-5-nitrobenzoic acid <strong>[612-19-1]2-Ethylbenzoic acid</strong> 1a (20.0 g, 133 mmol, prepared by a method disclosed in "") was added to 150 mL of sulfuric acid, then sodium nitrate (11.3 g, 133 mmol) was added in batches in an ice bath. The mixture was stirred for 3 hours, then N-bromosuccinimide (2.6 g, 14.5 mmol) was added in batches. The reaction system was stirred for 1 hour at 60C. After the reaction was completed, the reaction solution was poured to ice water, stirred well and filtered. The filtrate was washed with water, and concentrated under reduced pressure to obtain the crude title compound 3-bromo-2-ethyl-5-nitrobenzoic acid 1b (35 g) as a white solid, which was directly used in the next step without further purification.

Reference： [1]Patent: EP3378859,2018,A1 .Location in patent: Paragraph 0093; 0104-0105

44
[ 496-11-7 ]
[ 22927-13-5 ]
[ 767-90-8 ]
[ 83-33-0 ]
[ 612-19-1 ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 12194 - 12197

45
[ 930-68-7 ]
[ 612-19-1 ]
4-(4-ethyl-3-oxo-indan-1-yl)butanoic acid [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 6435 - 6439
Angew. Chem.,2019,vol. 131,p. 6501 - 6505,5

46
[ 4312-99-6 ]
[ 612-19-1 ]
7-ethyl-2-(3-oxooctyl)-2,3-dihydro-1H-inden-1-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 1348 - 1362

47
[ 122-57-6 ]
[ 612-19-1 ]
C₁₇H₁₆O [ No CAS ]

Reference： [1]ACS Catalysis,2019,vol. 9,p. 8153 - 8158

48
[ 4144-22-3 ]
[ 612-19-1 ]
C₁₇H₂₁NO₄ [ No CAS ]

Reference： [1]ChemCatChem,2019,vol. 11,p. 4116 - 4122

49
tert-butyl 3-amino-5-(3,5-dicyano-1,2,6-trimethyl-1,4-dihydropyridin-4-yl)-7-ethyl-6-fluoro-1H-indazole-1-carboxylate [ No CAS ]
[ 612-19-1 ]
N-[5-(3,5-dicyano-1,2,6-trimethyl-1,4-dihydropyridin-4-yl)-7-ethyl-6-fluoro-1H-indazol-3-yl]-2-ethylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%		tert-butyl 3-amino-5-(3,5-dicyano-1,2,6-trimethyl-1,4-dihydropyridin-4-yl)-7-ethyl-6-fluoro-1H-indazole-1-carboxylate (100 mg, 85 % purity, 189 pmol), HATU (100 mg, 264 pmol), and N,N-diisopropylethylamine (99 mI, 570 pmol), were dissolved in 3 ml_ of the N,N-dimethylformamide, the resulting mixture was stirred at room temperature for 15 min, then <strong>[612-19-1]2-<strong>[612-19-1]ethylbenzoic acid</strong></strong> (34.0 mg, 226 pmol) was added and the resulting mxiture was stirred at 90 C for 16 h. The resulting mixture was diluted by addition of water and extracted with ethyl acetate. The combined organic phases were washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo and the residue was purified by prep-HPLC (Column: XBridge Prep C18 OBD Column 19x150mm 5 pm; Mobile Phase A: Water (10 mmol/L NH4HC03), Mobile Phase B: ACN; Flow rate: 20 mL/min; Gradient: 25% B to 65% B in 7 min; Detector: 254 nm, 220 nm) to give 36.2 mg (38% yield) of the product as a light yellow solid. LC-MS [Water(0.05%TFA)-Acetonitrile, 5%B]: Rt = 1 .46 min. MS (ESIpos): m/z = 483 (M+H)+. 1H-NMR (400 MHz, DMSO-d6) d [ppm]: 1 .19-1 .26 (m, 6H), 2.27 (s, 6H), 2.79-2.92 (m, 4H), 3.20 (s, 3H), 4.66 (s, 1H), 7.29-7.36 (m, 2H), 7.43-7.46 (m, 1H), 7.51-7.58 (m, 2H), 10.77 (s, 1H), 13.01 (s, 1H).

Reference： [1]Patent: WO2019/185525,2019,A1 .Location in patent: Page/Page column 98-99

50
4-(3-amino-6-fluoro-7-methyl-1H-indazol-5-yl)-1,2,6-trimethyl-1,4-dihydropyridine-3,5-dicarbonitrile [ No CAS ]
[ 612-19-1 ]
N-[5-(3,5-dicyano-1,2,6-trimethyl-1,4-dihydropyridin-4-yl)-6-fluoro-7-methyl-1H-indazol-3-yl]-2-ethylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl acetamide; at 100℃; for 0.5h;	To a stirred solution of 4-(3-amino-6-fluoro-7-methyl-1H-indazol-5-yl)-1,2,6-trimethyl-1,4-dihydropyridine-3,5-dicarbonitrile (3.00 g, 8.92 mmol) in DMA (88 ml_) was added N,N-diisopropylethylamine (6.2 ml, 36 mmol), <strong>[612-19-1]2-<strong>[612-19-1]ethylbenzoic acid</strong></strong> (2.01 g, 13.4 mmol) and HATU (5.43 g, 14.3 mmol). The mixture was stirred at 100 C for 0.5 h. An aqueous solution of sodium bicarbonate was added, the mixture was stirred for 15 minutes and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate), filtered and the solvent was removed in vacuum. Silicagel chromatography followed by aminophase-silicagel chromatography gave a solid that was triturated with a mixture of dichloromethane and hexane to give 3.06 g (73 % yield) of the title compound. LC-MS (Method 2): Rt = 1 .1 1 min; MS (ESIpos): m/z = 469.5 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) d [ppm]: 0.831 (0.92), 0.837 (0.45), 0.854 (0.55), 0.859 (0.62), 1 .195 (1 .88), 1 .214 (4.10), 1 .233 (1 .97), 1.395 (0.59), 2.234 (16.00), 2.425 (3.33), 2.518 (0.86), 2.523 (0.56), 2.814 (0.96), 2.833 (0.92), 3.205 (9.22), 4.639 (1.87), 7.31 1 (0.48), 7.338 (0.55), 7.358 (0.69), 7.430 (0.48), 7.520 (0.46), 7.537 (0.41 ), 7.570 (0.61 ), 7.587 (0.61 ), 10.768 (0.60), 12.992 (1 .06).

Reference： [1]Patent: WO2019/185525,2019,A1 .Location in patent: Page/Page column 81

51
[ 667-27-6 ]
[ 612-19-1 ]
C₁₂H₁₄O₄ [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 8607 - 8610

52
[ 719-98-2 ]
[ 612-19-1 ]
C₁₀H₉F₃OS [ No CAS ]

Reference： [1]Chemical Science,2019,vol. 10,p. 9555 - 9559

53
6-amino-7-fluoro-3,4-dihydroquinolin-2(1H)-one [ No CAS ]
[ 612-19-1 ]
2-ethyl-N-(7-fluoro-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2h;	Into a 40-mL vial was placed a mixture of 6-amino-7-fluoro-3,4-dihydroquinolin-2(lH)-one (180 mg, 1.00 mmol, 1.00 equiv), N,N-dimethylformamide (5 mL), <strong>[612-19-1]2-<strong>[612-19-1]ethylbenzoic acid</strong></strong> (135 mg, 1.10 mmol, 1.10 equiv), N-ethyl-N-isopropylpropan-2-amine (387 mg, 3.00 mmol, 3.00 equiv) and l-((dimethylamino)(dimethyliminio)methyl)-lH-[l,2,3]triazolo[4,5-b]pyridine 3- oxide hexafluorophosphate(V) (570 mg, 1.50 mmol, 1.50 equiv). The reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was filtered and the filtrate was purified by prep-HPLC. This resulted in 181 mg (58%) of 2-ethyl-N-(7-fluoro-2-oxo-l, 2,3,4- tetrahydroquinolin-6-yl)benzamide as an off-white solid. LC-MS (ES) [M+l]+ m/r. 313.1. NMR (DMSO-£, 300 MHz) was consistent with a compound having the structure of 2- ethyl-N-(7-fluoro-2-oxo-l,2,3,4-tetrahydroquinolin-6-yl)benzamide.

Reference： [1]Patent: WO2020/28461,2020,A1 .Location in patent: Paragraph 00182

54
[ 74-88-4 ]
[ 612-19-1 ]
[ 50604-01-8 ]

Reference： [1]Organic and biomolecular chemistry,2020,vol. 18,p. 1567 - 1571

55
[ 719-64-2 ]
[ 107-06-2 ]
[ 612-19-1 ]
C₂₄H₂₁Cl₂NO₃ [ No CAS ]

Reference： [1]ChemCatChem,2020,vol. 12,p. 2721 - 2725

56
[ 767-90-8 ]
[ 612-19-1 ]

Reference： [1]Journal of Organic Chemistry,2020,vol. 85,p. 6181 - 6187

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P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
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. 612-19-1 ] {[proInfo.proName]}

Quality Control of [ 612-19-1 ]

Related Doc. of [ 612-19-1 ]

Product Details of [ 612-19-1 ]

Calculated chemistry of [ 612-19-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 612-19-1 ]

Application In Synthesis of [ 612-19-1 ]

[ 612-19-1 ] Synthesis Path-Upstream 1~2

[ 612-19-1 ] Synthesis Path-Downstream 1~56

Related Functional Groups of [ 612-19-1 ]

Aryls

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 612-19-1 ]