Chloroacetone → N-(3-nitrophenyl)-N-(2-oxo-propyl)-formamide

Participants

Reaction Steps

To a suspension of N-formyl-3-nitroaniline (1.0 g) in N,N-dimethylformamide (10 ml) was added sodium hydride (60% dispersion in mineral oil, 264 mg), and the mixture was stirred for 20 minutes under nitrogen atmosphere. After a solution of 1-chloropropan-2-one (0.573 ml) in N,N-dimethylformamide (5 ml) was added dropwise to the mixture, the mixture was stirred for 2 hours and diluted with ethyl acetate and water. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified with a silica gel column chromatography eluting with 2% methanol in dichloromethane to give N-(3-nitrophenyl)-N-(2-oxo-propyl)-formamide (280 mg, 21.0%).

Provenance & Evidence