Chloroacetyl chloride → Methyl 2-[(chloroacetyl)amino]benzoate

Participants

Reaction Steps

To a stirred solution of methyl 2-aminobenzoate (906 mg, 6.0 mmol) and NaHCO3 (554.4 mg, 6.6 mmol) in THF (12 mL) and water (12 mL) at 0° C. was added 2-chloroacetyl chloride (806 mg, 7.2 mmol) dropwise. After 2 hours, the mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure to afford the crude product. The residue was purified by flash chromatography to give methyl 2-(2-chloroacetamido)benzoate (1.31 g, 96%). LC-MS (ES-API); rt 8.65 min; m/z calculated for C10H10ClNO3 [M+Na]+ 250.0, found 250.0.

Provenance & Evidence