Acetyl chloride → Methyl 3-(acetylamino)-2-iodobenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-amino-2-iodobenzoate (70.0 g, 253 mmol) in methylene chloride (1000 mL) was added triethylamine (52.8 mL, 379 mmol) and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was added acetyl chloride (35.9 mL, 505 mmol) at 0° C. and the mixture was stirred at room temperature for 4 hr. The reaction mixture was diluted with water, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/10) to give the title compound (76.6 g, yield 95%).

Provenance & Evidence