Methanol → Methyl 3-amino-5-chlorobenzoate

To a stirred solution of 3-amino-5-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 (3×100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-amino-5-chloro-benzoic acid methyl ester (54 g, quant.) as a pale-white solid: LC/MS m/e calcd for C8H8ClNO2 (M+H)+: 186.61, observed: 185.9.

1. temperatureThen the mixture solution was refluxed for 12 hours
2. concentrationThen the reaction mixture was concentrated in vacuo
3. dissolutionthe residue was dissolved in ethyl acetate (500 mL)
4. washwashed with saturated aqueous sodium bicarbonate solution (3×100 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated in vacuo

ORD record

ord-2f0ceb59b9434c21b4af95af4f5e5229

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344137B2