ChemicalBook CAS DataBase List METHYL 4-AMINO-3-CHLOROBENZOATE

METHYL 4-AMINO-3-CHLOROBENZOATE synthesis

5synthesis methods

Product Name:METHYL 4-AMINO-3-CHLOROBENZOATE
CAS Number:84228-44-4
Molecular formula:C8H8ClNO2
Molecular Weight:185.61

67-56-1

2486-71-7

84228-44-4

Concentrated sulfuric acid (2.00 mL) was added slowly and dropwise to a stirred solution of 3-chloro-4-aminobenzoic acid (2.00 g, 11.7 mmol) in methanol (20.0 mL) at 0 °C. The reaction mixture was warmed to 80 °C and kept stirring for 6 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently concentrated under reduced pressure. The concentrated residue was diluted with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (2 x 50 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give methyl 4-amino-3-chlorobenzoate (2.10 g, 97% yield). The product was confirmed by NMR hydrogen spectroscopy (400 MHz, DMSO-d6): δ 7.70 (d, J = 1.6Hz, 1H), 7.58 (dd, J = 8.4, 2.0Hz, 1H), 6.77 (d, J = 8.8Hz, 1H), 6.24 (s, 2H), 3.73 (s, 3H).

67-56-1 Synthesis

67-56-1
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$7.29/5ml-f

2486-71-7 Synthesis

2486-71-7
206 suppliers
$8.00/1g

84228-44-4
138 suppliers
$7.00/1g

Yield: 100%

Reaction Conditions:

with thionyl chloride at 0; for 12 h;Reflux;

Steps:

112
Example 1128-Chloro-3 ,3 -dimethyl-2- (3 -morpholin-4-yl-phenyl)- 1 ,2,3 ,4-tetrahydro-quinoline-6- carboxylic acidTo a stirred solution of 4-amino-3-chloro-benzoic acid (50 g, 291 mmol) in methanol (300 mL) was added thionyl chloride (45 mL, 605 mmol) dropewise at 0 °C. Then the mixture solution was refluxed for 12 hours before cooling to room temperature. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate solution (3 x 100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 4-amino-3-chloro- benzoic acid methyl ester (54 g, quant.) as a pale-white solid: LC/MS m/e calcd for C₈H₈C1N0₂ (M+H)⁺: 186.61, observed: 185.9.

References:

F. HOFFMANN-LA ROCHE AG;CHEN, Li;FENG, Lichun;HUANG, Mengwei;LIU, Yongfu;WU, Guolong;WU, Jim, Zhen;ZHOU, Mingwei WO2011/128251, 2011, A1 Location in patent:Page/Page column 203

619-45-4 Synthesis