Methylamine → 2-(3-bromophenyl)-N-methylacetamide

Participants

Reaction Steps

A mixture of 3-bromophenylacetic acid (3.02 g), a solution (2.0 M; 8.5 ml) of methylamine in THF, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (3.20 g), 1-hydroxybenzotriazole (2.60 g) and triethylamine (2.3 ml) was stirred in DMF (30 ml) at room temperature for 24 h. The reaction mixture was diluted with ethyl acetate, washed successively with water, 1N aqueous sodium hydroxide solution, 1N hydrochloric acid, aqueous sodium hydrogen carbonate and brine, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was purified by silica gel chomatography (eluent; ethyl acetate). Recrystallization from hexane-ethyl acetate gave the title compound (1.30 g) as colorless prism crystals.

Provenance & Evidence