Methylamine → Methyl 4-(methylamino)carbonyl-3-nitrobenzoate

Participants

Reaction Steps

A mixture of 4-methoxycarbonyl-2-nitrobenzoic acid (3.6 g, 0.016 mol) in thionyl chloride (32 mL) was heated to reflux in the presence of two drops of dimethylformamide for 3 h. Thionyl chloride was distilled and the concentrate was left under vacuum for 0.5 h. The residue was dissolved in dichloromethane (10 mL) and added to a solution of aqueous methylamine (40%, 2.0 g, 0.026 mol) in water (5 mL) over a period of 5 min. The mixture was further stirred for 10 min and the white precipitate was collected by filtration. The cake was washed with water, dried, and recrystallized from ethyl acetate-hexane to give 2.1 g (55%) of methyl 4-(methylamino)carbonyl-3-nitrobenzoate as white needles, mp 155° C.

Provenance & Evidence