Methyl 5-chloroanthranilate synthesis
- Product Name:Methyl 5-chloroanthranilate
- CAS Number:5202-89-1
- Molecular formula:C8H8ClNO2
- Molecular Weight:185.61
Yield:5202-89-1 100%
Reaction Conditions:
with thionyl chloride at 0; for 12 h;Reflux;
Steps:
100
Example 1006-Chloro-3 ,3 -dimethyl-2- (3 -morpholin-4-yl-phenyl)- 1 ,2,3 ,4-tetrahydro-quinoline-8- carboxylic acidTo a stirred solution of 2-amino-5-chloro-benzoic acid (50 g, 291 mmol) in methanol (300 mL) was added thionyl chloride (45 mL, 605 mmol) dropwise 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 2-amino-5-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 187
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