Chlorosuccinimide → 2-Amino-5-chloro-3-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-amino-3-methylbenzoic acid (Aldrich, 15.0 g, 99.2 mmol) in N,N-dimethylformamide (50 mL) was added N-chlorosuccinimide (13.3 g, 99.2 mmol) and the reaction mixture was heated to 100° C. for 30 minutes. The heat was removed and the reaction mixture was cooled to room temperature and allowed to stand overnight. The reaction mixture was then slowly poured into ice water (250 mL) to precipitate a white solid. The solid was filtered and washed four times with water and then taken up in ethyl acetate (900 mL). The ethyl acetate solution was dried (MgSO4) and evaporated under reduced pressure, and the residual solid was washed with ether to afford the desired intermediate as a white solid, 13.9 g (75.4% yield).

Provenance & Evidence