35613-44-6|Methyl 2-(2-aminophenyl)acetate| Ambeed

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Quality Control of [ 35613-44-6 ] Purity: 96% SDS Specification

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Product Details of [ 35613-44-6 ]

CAS No. :	35613-44-6
Formula :	C₉H₁₁NO₂
M.W :	165.19
SMILES Code :	COC(=O)CC1=C(N)C=CC=C1
MDL No. :	MFCD04973395
InChI Key :	BWQBYHGDMBHIIQ-UHFFFAOYSA-N
Pubchem ID :	5743389

Safety of [ 35613-44-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 35613-44-6 ]

* 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.

Downstream synthetic route of [ 35613-44-6 ]

[ 35613-44-6 ] Synthesis Path-Downstream 1~35

1
[ 30095-98-8 ]
[ 35613-44-6 ]

Yield	Reaction Conditions	Operation in experiment
98%	With palladium on activated charcoal; hydrogen; In toluene; at 5℃; under 760.051 Torr;	Compound 2 (97.6 g, 0.5 mol),Pd/C (0.98g) and toluene (200mL) were placed in the reaction flask.Hydrogen was passed through a hydrogenation reaction at normal pressure of 5 C overnight.After the reaction,filter,Wash with a small amount of toluene,Combine the filtrate and the wash solution,Recovering toluene,Precipitating solids,Vacuum drying,The pale yellow liquid was Intermediate 3 (80.9 g, 98%).
97%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃;	Preparation of methyl 2-(2-aminophenyl)acetate (Compound 6-1) [00231j A mixture of Compound 1-2 (9.75 g, 50 mmol), 10% palladiumlactivecarbon catalyst (dry, 530 mg, 5 mmol) in methanol (100 mL) was stirred under hydrogen atmosphere at room temperature for overnight. The reaction mixture was filtered to remove palladiumlactive carbon catalyst and the filtrate was concentrated to give Compound 6-1 (8.02 g, yield: 97%) as a pale yellow oil. MS (ES): mlz:166[M+H]. ?H NMR (400 MHz, DMSO-d6) oe: 6.94 (m, 2H), 6.64 (d, 1H, J 8.0 Hz),6.51 (m, 1H), 4.88 (s, 2H), 3.59 (s, 3H), 3.52 (s, 2H).
97%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 760.051 Torr;	Preparation of methyl 2-(2-aminophenyl)acetate (Compound 11-3)[00269j A mixture of methyl 2-(2-nitrophenyl)acetate (Compound 11-2, 9.75 g, 50 mmol), 10% palladiumlactive carbon catalyst (dry, 530 mg, 5 mmol) in methanol (100 mL) was stirred under H2 (1 atm.) at room temperature overnight. The reaction mixture was filtered to remove palladiumlactive carbon catalyst and the filtrate was concentrated to give the desired product methyl 2-(2-aminophenyl)acetate (Compound 11-3, 8.02 g, yield: 97%) as a pale yellow oil. MS (ESI): mlz: 166[M+H]. ?H NMR (400 MHz, DMSO-d6) oe: 6.94 (m, 2H), 6.64 (d, 1H, J= 8.0 Hz), 6.51 (m, 1H), 4.88 (s, 2H), 3.59 (s, 3H), 3.52 (s, 2H).

67%	With hydrogen;palladium 10% on activated carbon; In ethyl acetate; at 20℃; for 2h;	The 2-nitrophenyl acid methyl ester (1 g, 5.13 mmol) was dissolved in 20 mL of EA and 0.3 g of Pd/C 10% was suspended into the solution, the reaction mixture was under hydrogen atmosphere at room temperature. After 2h the reaction was completed by TLC analysis (DCM: EA 60; 40) the Pd/C 10% was removed by filtration and the solvent by reduced pressure; to yield a colorless oil 0.67 g (67%).
8.5 g (100%)	palladium-carbon; In methanol;	B. Methyl 2-aminophenylacetate. Methyl 2-nitrophenylacetate (10.1 g, 51.2 mmol) in 125 mL of methanol containing 221 mg of 10% Pd/C was placed on the Parr hydrogenator at 40 psi. After 5 h the mixture was filtered through celite and evaporated under reduced pressure to give a clear red oil. The solvent was evaporated under reduced pressure to give 8.5 g (100%) of methyl 2-aminophenylacetate as a clear red oil. TLC (silica, EtOAc/hexanes): Rf=0.24. 1H NMR (400MHz, CDCl3): 7.21 (m, 2H), 6.86 (m, 2H), 3.81 (s, 3H), 3.70 (s, 2H).
	With hydrogen;platinum(IV) oxide; In methanol; under 2585.81 - 2844.39 Torr; for 25.5h;	B. (2-Amino-phenyl) acetic acid methyl ester; The title A compound, (2-nitro-phenyl)-acetic acid methyl ester (5.0 g, 25.6 mmol) is dissolved in MeOH (125 mL) in a Parr Bottle. It is purged with nitrogen, then added Pt02 (185 mg), then placed on a Parr Shaker under 50 to 55 psi of hydrogen with shaking for 25.5 h. The reaction is opened and filtered through celite, and concentrated to yield (2-amino- phenyl) acetic acid methyl ester as an amber oil : [M+1] + = 166.
	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃;Inert atmosphere;	Add Pd/C (10%, 800 mg) to a solution of methyl 2-(2-nitrophenyl)acetate (7.5 g, 38.5 mmol) in methanol (50 mL) under N2, then flush with H2, stir the reaction under atmosphere at room temperature overnight. Remove the hydrogen; filter off the solid, concentrate the filtrate under reduced pressure to obtain the crude product (4.8 g, 76.2%) which is used directly without further purification. MS: (M+l):166
	With palladium 10% on activated carbon; hydrogen; In methanol; at 25℃;Inert atmosphere;	Add Pd/C (10%, 800 mg) to a solution of methyl 2-(2-nitrophenyl)acetate (7.5 g, 38.5 mmol) in methanol (50 mL) under N2, then flush with H2, stir the reaction under H2 atmosphere at room temperature overnight. Remove the hydrogen; filter off the solid, concentrate the filtrate under reduced pressure to obtain the crude product (4.8 g, 76.2%) which is used directly without further purification. MS: (M+1):166.

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 691 - 701.
[2]Angewandte Chemie - International Edition,2019,vol. 58,p. 7861 - 7865.
Angew. Chem.,2019,vol. 131,p. 7943 - 7947,5.
[3]European Journal of Organic Chemistry,2017,vol. 2017,p. 1889 - 1893.
[4]Patent: CN108947861,2018,A .Location in patent: Paragraph 0025-0026.
[5]Patent: WO2014/106238,2014,A1 .Location in patent: Paragraph 00231.
[6]Patent: WO2014/106238,2014,A1 .Location in patent: Paragraph 00269; 00397.
[7]Patent: WO2009/3970,2009,A1 .Location in patent: Page/Page column 42-43.
[8]Journal of the American Chemical Society,1937,vol. 59,p. 2348,2350.
[9]Journal of the American Chemical Society,1983,vol. 105,p. 74 - 79.
[10]Journal of Organic Chemistry,1995,vol. 60,p. 2326 - 2327.
[11]Tetrahedron,1997,vol. 53,p. 16521 - 16532.
[12]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2891 - 2893.
[13]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4396 - 4401.
[14]Patent: US2005/101587,2005,A9 .
[15]Patent: WO2003/82841,2003,A1 .Location in patent: Page/Page column 90.
[16]Journal of Organic Chemistry,2009,vol. 74,p. 9222 - 9224.
[17]Patent: WO2014/418,2014,A1 .Location in patent: Page/Page column 60.
[18]RSC Advances,2014,vol. 4,p. 44629 - 44633.
[19]Patent: US2015/197511,2015,A1 .Location in patent: Paragraph 0294; 0295.
[20]European Journal of Organic Chemistry,2015,vol. 2015,p. 5775 - 5780.

2
[ 35613-44-6 ]
[ 67-56-1 ]
[ 59-48-3 ]

References: [1]Chemische Berichte,1922,vol. 55,p. 839.

3
[ 30095-98-8 ]
[ 59-48-3 ]
[ 35613-44-6 ]

References: [1]Liebigs Annalen der Chemie,1985,vol. 1985,p. 1398 - 1412.
[2]Organic Letters,2009,vol. 11,p. 1345 - 1348.

4
[ 35613-44-6 ]
[ 59-48-3 ]

Yield	Reaction Conditions	Operation in experiment
4 g	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;	Stir the mixture of <strong>[35613-44-6]methyl 2-(2-aminophenyl)acetate</strong> (4.8 g, 29.1 mmol) and potassium carbonate (8.0 g, 58.2 mmol) in DMF (15 mL) at room temperature overnight. TLC (PE:EtOAc=2:l) shows the reaction is complete. Concentrate the reaction mixture under reduced pressure to give the crude product. Purify by chromatography (silica gel, EtOAc:PE=l:2) to afford the title compound (4.0 g, 95%). MS: (M+l): 134.2.
4 g	With potassium carbonate; In N,N-dimethyl-formamide; at 25℃;	Stir the mixture of <strong>[35613-44-6]methyl 2-(2-aminophenyl)acetate</strong> (4.8 g, 29.1 mmol) and potassium carbonate (8.0 g, 58.2 mmol) in DMF (15 mL) at room temperature overnight. TLC (PE:EtOAc=2:1) shows the reaction is complete. Concentrate the reaction mixture under reduced pressure to give the crude product. Purify by chromatography (silica gel, EtOAc:PE=1:2) to afford the title compound (4.0 g, 95%). MS: (M+1): 134.2.

References: [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 4505 - 4510.
Angew. Chem.,2020,vol. 132,p. 4535 - 4540,6.
[2]Journal of the American Chemical Society,1983,vol. 105,p. 74 - 79.
[3]Journal of the American Chemical Society,1983,vol. 105,p. 74 - 79.
[4]Patent: WO2014/418,2014,A1 .Location in patent: Page/Page column 60.
[5]Patent: US2015/197511,2015,A1 .Location in patent: Paragraph 0296; 0297.
[6]European Journal of Organic Chemistry,2015,vol. 2015,p. 5775 - 5780.

5
[ 1953-56-6 ]
[ 35613-44-6 ]
[ 163776-49-6 ]

References: [1]Journal of Organic Chemistry,1995,vol. 60,p. 2326 - 2327.
[2]Tetrahedron,1997,vol. 53,p. 16521 - 16532.

Yield	Reaction Conditions	Operation in experiment
93.0%		(B) Methyl 2-(2-aminophenyl)acetate The methyl 2-(2-nitrophenyl)acetate obtained in (A) (1.69 g, 8.66 mmol) was dissolved in methanol (20 ml). 10% palladium/carbon (0.17 g) was suspended in the solution, and the suspension was stirred at room temperature under hydrogen atmosphere (1 atm) for 19 hours. The catalyst was removed by filtration and washed with methanol, and then the solvent was evaporated to obtain the title compound as pale orange oil (1.33 g, 93.0%). 1H-NMR (CDCl3) delta: 3.57 (2H, s), 3.68 (3H, s), 4.06 (2H, br), 6.67-6.79 (2H, m), 7.04-7.12 (2H, m)

8
[ 35613-44-6 ]
methyl (3S)-(-)-7-chloro-3-carboxymethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylate [ No CAS ]
[ 502481-66-5 ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 691 - 701.

9
[ 35613-44-6 ]
[ 1479-24-9 ]
[ 606922-11-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2891 - 2893.

10
[ 35613-44-6 ]
[ 94-02-0 ]
[ 606922-10-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2891 - 2893.

11
[ 35613-44-6 ]
[ 33166-77-7 ]
[ 861230-04-8 ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4396 - 4401.

12
[ 35613-44-6 ]
[ 79099-07-3 ]
[ 400797-94-6 ]

Yield	Reaction Conditions	Operation in experiment
42%		Preparation of tert-butyl 4-(2-oxoindolin- 1 -yl)piperidine- 1 -carboxylate (Compound 6-2) [00232j A mixture of Compound 6-1 (3.30 g, 20 mmol), tert-butyl 4-oxopiperidine-1-carboxylate (4.38 g, 22 mmol), acetic acid (HOAc, 600 mg, 10 mmol) in dichloromethane (DCM, 80 mL) was stirred at room temperature for 2 h, then sodium triacetoxyborohydride (6.36 g, 30 mmol) was added in portions and heated to 40C, stirred overnight. The reaction mixture was cooled to room temperature and diluted with dichloromethane (200 mL), washed with water (200 mL x 2) and sodium bicarbonate (sat. aq., 200 mL x 2), dried over anhydrous sodium sulfate, concentrated to give the crude product, purified by column chromatography on silica gel (ethyl acetate in petroleum ether, 5%, V/v) to give Compound 6-2 (2.65 g, yield: 42%) as a white solid. MS (ES): mlz: 261[M+H-56]. ?H NMR (400 MHz, CDC13) oe: 7.24 (m, 2H), 7.01 (m, 2H), 4.41 (m, 1H), 4.28 (br s, 2H), 3.53 (s, 2H), 2.83 (br s, 2H), 2.32 (m, 2H), 1.70 (m, 2H), 1.50 (s, 9H).
42%		Preparation of tert-butyl 4-(2-oxoindolin- 1 -yl)piperidine- 1 -carboxylate (Compound 11-4) [00270j A mixture of <strong>[35613-44-6]methyl 2-(2-aminophenyl)acetate</strong> (Compound 11-3, 3.30 g, 20 mmol), tert-butyl 4-oxopiperidine-1-carboxylate (4.38 g, 22 mmol), acetic acid (HOAc, 600 mg, 10 mmol) in dichloromethane (DCM, 80 mL) was stirred at room temperature for 2 h, then sodium triacetoxyborohydride (NaBH(OAc)3, 6.36 g, 30 mmol) was added in portions and heated to 40C, stirred overnight. The reaction mixture was cooled to room temperature and diluted with dichloromethane (DCM, 200 mL), washed with water (200 mL x 2) and sodium bicarbonate (sat. aq., 200 mL x 2), dried over anhydrous sodium sulfate, concentrated to give the crude product, purified by flash colunm chromatography on silica gel (ethyl acetate petroleum ether, 1 20-1 15-1 10 v v) to give the desired product tert-butyl 4-(2-oxoindolin- 1 -yl)piperidine- 1- carboxylate (Compound 11-4, 2.65 g, yield: 42%) as a pale yellow solid. MS (ESI):mlz: 261[M+H-56]. ?H NMR (400 MHz, CDC13) oe: 7.24 (m, 2H), 7.01 (m, 2H), 4.41 (m, 1H), 4.28 (br s, 2H), 3.53 (s, 2H), 2.83 (br s, 2H), 2.32 (m, 2H), 1.70 (m, 2H), 1.50 (s, 9H).
3.9 g (62%)	With sodium tris(acetoxy)borohydride; sodium hydrogencarbonate; acetic acid; In dichloromethane;	C. 4-(2-Oxo-2.3-dihydro-indol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester. Methyl 2-aminophenylacetate (3.0 g, 18.2 mmol) and 1-tert-butoxycarbonyl-4-piperidone (4.5 g, 22.6 mmol) were set stirring in 50 mL of CH2Cl2 under an atmosphere of nitrogen. Sodium triacetoxyborohydride (5.4 g, 25.5 mmol) was added followed by 1 mL of acetic acid. After 20 h at rt the mixture was quenched by the slow addition of saturated NaHCO3. After stirring for 30 min, the organics were separated, dried (MgSO4), and evaporated to afford 7.5 g of a purple oil. Purification by column chromatography (silica, 10-50% EtOAc/hexanes) gave 3.9 g (62%) of the title compound. TLC (silica, 25% EtOAc/hexanes): Rf=0.15. 1H NMR (400MHz, CDCl3): 7.25 (m, 2H), 7.01 (m, 2H), 4.40 (m, 1H), 3.53 (s, 2H), 2.83 (m, 2H), 2.32 (m, 2H), 1.70 (m, 2H), 1.51 (s, 9H).

References: [1]Patent: WO2014/106238,2014,A1 .Location in patent: Paragraph 00232; 00314; 00341; 00365; 00398; 00499.
[2]Patent: WO2014/106238,2014,A1 .Location in patent: Paragraph 00270.
[3]Patent: US2005/101587,2005,A9 .

13
[ 5292-43-3 ]
[ 35613-44-6 ]
[ 612531-38-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 50℃; for 19h;	C. [2- (t-Butoxycarbonylmethyl-amino)-phenyl]-acetic acid methyl ester; The title B compound, (2-amino-phenyl) acetic acid methyl ester (4.2 g, 25.4 mmol) is dissolved in DMF (30 mL). Powdered potassium carbonate (8.78 g, 63.5 mmol) and t-butyl bromoacetate (4.12 mL, 27.9 mmol) are added and the reaction is stirred at room temperature for 18 h and then at 50C for 1 h. The reaction is diluted with water (300 mL) and extracted with EtOAc (2 x 200 mL). Combined EtOAc layers are washed with water (2 x 100 mL) then brine (100 mL), dried over anhydrous MgS04, filtered and concentrated to give a viscous brown oil. This residue is chromatographed on a 110 g silica gel RediSep (Isco Inc.) column with a 30 mUmin gradient elution of 10: 90 (EtOAc: hexane) to 25: 75 over 30 min. Fractions containing product are combined and evaporated to yield [2-(t-butoxy- carbonylmethyl-amino)-phenyl]-acetic acid methyl ester as a clear amber oil : [M+1] + = 280.

References: [1]Patent: WO2003/82841,2003,A1 .Location in patent: Page/Page column 90.

14
[ 3740-52-1 ]
[ 35613-44-6 ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4396 - 4401.
[2]Tetrahedron,1997,vol. 53,p. 16521 - 16532.
[3]Journal of the American Chemical Society,1983,vol. 105,p. 74 - 79.
[4]Journal of the American Chemical Society,1937,vol. 59,p. 2348,2350.
[5]Patent: WO2014/418,2014,A1 .
[6]Patent: WO2014/106238,2014,A1 .
[7]RSC Advances,2014,vol. 4,p. 44629 - 44633.
[8]Patent: US2015/197511,2015,A1 .
[9]European Journal of Organic Chemistry,2017,vol. 2017,p. 1889 - 1893.
[10]Angewandte Chemie - International Edition,2019,vol. 58,p. 7861 - 7865.
Angew. Chem.,2019,vol. 131,p. 7943 - 7947,5.

15
[ 35613-44-6 ]
[2-(3-fluoro-phenyl)-4-oxo-1,4-dihydro-quinolin-8-yl]-acetic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 4396 - 4401.

16
[ 3740-52-1 ]
resin bound 1-aminomethylnaphthalene [ No CAS ]
[ 35613-44-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2891 - 2893.

17
[ 35613-44-6 ]
[ 125421-32-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2891 - 2893.

18
[ 35613-44-6 ]
[2-(2-fluoro-phenyl)-4-oxo-1,4-dihydro-quinolin-8-yl]-acetic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 2891 - 2893.

19
[ 35613-44-6 ]
3-[(2-carboxymethyl-phenylcarbamoyl)-methyl]-7-chloro-1,3,4,5-tetrahydro-benzo[<i>cd</i>]indole-2-carboxylic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 691 - 701.

20
[ 35613-44-6 ]
[ 200122-22-1 ]

References: [1]Tetrahedron,1997,vol. 53,p. 16521 - 16532.

21
[ 35613-44-6 ]
[ 163776-50-9 ]

References: [1]Tetrahedron,1997,vol. 53,p. 16521 - 16532.

22
[ 35613-44-6 ]
[ 163776-51-0 ]

References: [1]Tetrahedron,1997,vol. 53,p. 16521 - 16532.

23
[ 30095-98-8 ]
[ 35613-44-6 ]
[ 124-63-0 ]
methyl 2-(methylsulfonylamino)phenylacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium sulfate; triethylamine;palladium; In toluene;	To a solution of methyl 2-nitrophenylacetate, (6.04 kg) in toluene (100 l) is added anhydrous magnesium sulfate (2.00 kg) and then 5% palladium-on-charcoal (125 g). The mixture is then stirred and hydrogenated, keeping the temperature below 40 by regulation of the stirring rate and input of hydrogen gas. After the addition is complete, the mixture is filtered. The filtrate containing <strong>[35613-44-6]methyl 2-aminophenylacetate</strong> is cooled to -20 and triethylamine (3.75 kg) is added all at once with stirring. This is followed by the slow addition of a solution of methanesulfonyl chloride (3.91 kg) in toluene (4.5L), keeping the temperature between -2 and 5. After stirring at -2 for 1 hour, the mixture is filtered and washed with toluene (10 l). The filter cake is then slurried with water (90 l) for 90 minutes, filtered, and washed with water (45 l) and methanol (8 l). The solid is dried at 50 in vacuo overnight to yield methyl 2-(methylsulfonylamino)phenylacetate, mp 73-75.

References: [1]Patent: US4803197,1989,A .

Yield	Reaction Conditions	Operation in experiment
59.4%		(C) Methyl 2-(2-[(trifluoromethyl)sulfonyl]aminophenyl)acetate The methyl 2-(2-aminophenyl)acetate obtained in (B) (1.32 g, 7.99 mmol) was dissolved in methylene chloride (50 ml), and the solution was added dropwise with triethylamine (1.23 ml, 8.79 mmol) under ice cooling, and slowly added dropwise with trifluoroacetic anhydride (1.34 ml, 7.99 mmol). After the reaction mixture was stirred for 15 minutes at the same temperature, the organic layer was separated, and the layer was washed with 10% aqueous citric acid, saturated aqueous sodium hydrogencarbonate and then with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain the title compound as pale orange oil (1.41 g, 59.4%). 1H-NMR (CDCl3) delta: 3.75 (2H, s), 3.77 (3H, s), 7.17-7.45 (3H, m), 7.48-7.65 (1H, m)

25
[ 35613-44-6 ]
[ 445306-08-1 ]
[ 1131987-44-4 ]

References: [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 2955 - 2967.

26
[ 347877-90-1 ]
[ 35613-44-6 ]

References: [1]Tetrahedron,2008,vol. 64,p. 5531 - 5540.

27
[ 347877-90-1 ]
[ 35613-44-6 ]
[ 1037296-82-4 ]

References: [1]Tetrahedron,2008,vol. 64,p. 5531 - 5540.

28
[ 86-98-6 ]
[ 35613-44-6 ]
[ 25553-00-8 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; for 24h;Heating / reflux;	A mixture of 160 g of 4,7-dichloroquinoline, 80 g of <strong>[35613-44-6]methyl 2-aminophenylacetate</strong> and 500 mL of acetonitrile is heated at reflux temperature for 24 hours. The solvent is evaporated under reduced pressure and the residue extracted 4 times with 750 mL portions of hot water. The aqueous extract is rendered basic (pH 8) with 10% ammonium hydroxide whereupon [2- (7-Chloro-quinolin-4-ylamino)-phenyl]-acetic acid methyl ester separates as an oil which crystallizes upon addition of ethanol. The product may be recrystallized from aqueous methanol, M.P.147-148C.[0114] The hydrochloride of £2-(7-Chloro-quinolin-4-ylamino)-phenyl]-acetic acid methyl ester may be prepared in conventional manner by treating a solution of the free base in ether with gaseous hydrochloric acid; M.P. 224-226C. [0115] To a solution of 6 g of [2-(7-Chloro-quinolin-4-ylamino)-phenyl]-acetic acid methyl ester in 100 mL of hot methanol is added 3 g of methanesulfonic acid. The solution is cooled to room temperature and 750 mL of ether is added. The product precipitates as off-white crystals and is collected by filtration. The resulting methanesulfonate of the above-mentioned compound is recrystallized from methanol-ether, M.P. 179-1810C.

References: [1]Patent: WO2008/48577,2008,A1 .Location in patent: Page/Page column 33.

29
[ 346-55-4 ]
[ 35613-44-6 ]
[ 25560-46-7 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; for 18h;Heating / reflux;	A mixture of 7.2 g of 4-chloro-7-trifluoromethylquinoline, 5.4 g of methyl 2- aminophenylacetate and 250 mL of acetonitrile is heated under reflux for 18 hours. The solvent is evaporated under reduced pressure and the residue extracted 3 times with 200 mL portions of hot water. The aqueous extract is rendered basic with 10% ammonium hydroxide whereupon the desired compound precipitated; it was recrystallized from aqueous ethanol yielding colorless needles with a melting point of 140-1410C.

References: [1]Patent: WO2008/48577,2008,A1 .Location in patent: Page/Page column 33.

30
[ 98-31-7 ]
[ 35613-44-6 ]
[ 36659-86-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With pyridine; In dichloromethane;	2-(2-(3,4-Dichlorophenylsulfonamido)phenyl)acetic acid methyl ester; 2-Aminophenylacetic acid methyl ester (10.2 g, 39.45 mmol) was dissolved in DCM (200 ml). There were then added first pyridine (12.4 ml, 151.71 mmol) and 3,4-dichlorobenzenesulfonyl chloride (11.8 ml, 75.87 mmol) in DCM (50 ml). The reaction solution was stirred overnight and then diluted with DCM and washed in succession with 0.5 M KHSO4 solution, saturated NaHCO3 solution and saturated NaCl solution, dried over sodium sulfate and concentrated. Purification was carried out by column chromatography on silica gel (DCM).Yield: 14.3 g (96%)

References: [1]Patent: US2008/312231,2008,A1 .Location in patent: Page/Page column 37.

31
[ 67-56-1 ]
[ 3342-78-7 ]
[ 35613-44-6 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; at 0 - 20℃;	2-(2-(3,4-Dichloro-N-methylphenylsulfonamido)phenyl)-acetic acid S2; Thionyl chloride (5.2 ml, 71.4 mmol) was added dropwise, with stirring and while cooling with ice, to a solution of 2-aminophenylacetic acid (7.2 g, 47.6 mmol) in methanol (150 ml). The reaction mixture was stirred overnight at room temperature. The reaction solution was concentrated, and thionyl chloride residues were removed by dragging out with toluene and DCM. 10.3 g (contaminated with starting material) of the were obtained in the form of a brown solid. The crude product was used further without being purified further.

References: [1]Patent: US2008/312231,2008,A1 .Location in patent: Page/Page column 37.

32
[ 35613-44-6 ]
C₉H₉N₂O₂⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium nitrite; In water; at -5℃;Cooling with acetone/ice;	The 2-aminophenyl acid methyl ester (3 g, 0.018 mol) was dissolved in water(4OmL) with concentrated HCl (9 mL) and the solution was cooled in an ice/acetone bath to -5 0C, afterward sodium nitrite (1.32 g, 0.019 mol) in ImL of water was added dropwise. At that point the diazonium salt was formed and the solution took a pale yellow color. A spatula of urea was added to neutralize the excess of sodium nitrite (oxidant) and the diazonium salt solution was added dropwise into a solution of phenol (1.68 g, 0.018 mol), sodium acetate (2.88 g, 0.036 mol) and ammonia solution (5 mL) in water (40 mL), which was at -5 0C, after 5 minutes. After the addition was done glacial acetic acid (eq, 5 mL) was added and the reaction mixture was filtered. The filter cake was dissolved in EA and dried over sodium sulfate, the solvent removed under reduced pressure and the product purified by flash chromatography (DCM 100 mL, DCM: EA 80: 20) to yield 2.7 g (56%): m.p. 158- 160 0C, IRvm(rc(KBr): 3221.84 (OH), 1695.48 (C=O) cm"1. 1H-NMR (400MHz, Acetone) delta: 9.14 (IH, s), 7.86 (2H, d, J 8.50 Hz), 7.72 (IH, d, J 8 Hz), 7.45 (3H, m, J 7.52 Hz), 7.03 (2H, d, J 8.50 Hz), 4.16 (2H, s), 3.62 (3H, s). 13C-NMR (400MHz, Acetone) delta: 204.91 (C=O, Acetone), 171.22 (C=O, C-8), 160.29 (C, C-4'), 149.64 (c, C-2), 146.20 (C, C-I '), 134.13 (CH, C-6), 131.13 (CH, C-5), 129.97 (QC-I), 127.42 (CH, C-4), 124.65 (CH,C-3, C-6', C-2'), 115.38 (CH, C-5'), 114.73 (CH, C-3'), 50.65 (CH3, C-9), 36.41 (CH2, C-7), 28.52 (Acetone, CH3).

References: [1]Patent: WO2009/3970,2009,A1 .Location in patent: Page/Page column 42-43.

33
[ 98-01-1 ]
[ 35613-44-6 ]
[ 1198328-65-2 ]

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 9222 - 9224.

34
[ 35613-44-6 ]
[ 104-87-0 ]
[ 1198328-56-1 ]

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 9222 - 9224.

35
[ 35613-44-6 ]
[ 104-88-1 ]
[ 117239-86-8 ]

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 9222 - 9224.

Historical Records

Technical Information

• Acyl Group Substitution • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bouveault-Blanc Reduction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • Ester Cleavage • Friedel-Crafts Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Alkylbenzene • Preparation of Amines • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction • Vilsmeier-Haack Reaction

Related Functional Groups of
[ 35613-44-6 ]

Aryls

A186904 [52913-11-8]

Methyl 2-(3-aminophenyl)acetate

Similarity: 0.98

A142008 [150319-83-8]

Methyl 2-(3-aminophenyl)acetate hydrochloride

Similarity: 0.96

A453155 [52273-79-7]

Ethyl 2-(3-aminophenyl)acetate

Similarity: 0.94

A527304 [850449-93-3]

Methyl 2-(5-amino-2-methylphenyl)acetate

Similarity: 0.94

A316974 [5438-70-0]

Ethyl 4-aminophenylacetate

Similarity: 0.92

Esters

A186904 [52913-11-8]

Methyl 2-(3-aminophenyl)acetate

Similarity: 0.98

A142008 [150319-83-8]

Methyl 2-(3-aminophenyl)acetate hydrochloride

Similarity: 0.96

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Ethyl 2-(3-aminophenyl)acetate

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A527304 [850449-93-3]

Methyl 2-(5-amino-2-methylphenyl)acetate

Similarity: 0.94

A316974 [5438-70-0]

Ethyl 4-aminophenylacetate

Similarity: 0.92

Amines

A186904 [52913-11-8]

Methyl 2-(3-aminophenyl)acetate

Similarity: 0.98

A142008 [150319-83-8]

Methyl 2-(3-aminophenyl)acetate hydrochloride

Similarity: 0.96

A453155 [52273-79-7]

Ethyl 2-(3-aminophenyl)acetate

Similarity: 0.94

A527304 [850449-93-3]

Methyl 2-(5-amino-2-methylphenyl)acetate

Similarity: 0.94

A316974 [5438-70-0]

Ethyl 4-aminophenylacetate

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CAS No.: 35613-44-6

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