Hydrochloric Acid → 2-chloro-N-methoxy-N,4-dimethylbenzamide

Participants

Reaction Steps

1.25 g (6.61 mmol) of 2-chloro-4-methylbenzoyl chloride in 4 ml of dichloromethane were mixed with 0.84 g (8.60 mmol) of N,O-dimethylhydroxylamine hydrochloride and 2.4 ml (17.2 mmol) of triethylamine and stirred for 24 h. Water and 1N hydrochloric acid were added to the reaction mixture, the phases were separated, and the aqueous phase was extracted twice with dichloromethane. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient) to result in 1.10 g (78% of theory) of the title compound.

Provenance & Evidence