Methylamine → trans 3-bromo-N-methylcinnamamide

Participants

Reaction Steps

A solution of trans 3-bromocinnamoyl chloride (5 g) in dry benzene (100 ml) was added with stirring to an ethereal (200 ml) solution of methylamine (3 g). After the addition was complete, a slow stream of methylamine gas was bubbled through the reaction mixture at room temperature for 1 hour. Solvent and excess amine were removed under reduced pressure. The crude product was triturated with water, filtered, and recrystallized from ethanol-water to give trans 3-bromo-N-methylcinnamamide, m.p. 147°-147.5° C. NMR, IR, and elemental analysis were consistent with this structure.

Provenance & Evidence