Water → 3-Anilino-2-(4-methoxy--naphthylmethyl)acrylonitrile

Participants

Reaction Steps

To a solution of 4-methoxy-1-naphthaldehyde (10.0 g, 53.7 mmol) and 3-anilinopropionitrile (9.0 g, 61.6 mmol) in dimethylsulfoxide (25 mL) was added a solution of sodium methoxide (2.9 g, 53.6 mmol) in methanol (25 mL). The resulting mixture was heated to 133° with distillation of the methanol over 45 min. The reaction was then cooled, diluted with ethanol:water and the precipitate that formed was collected, washed with water, ethanol and hexane to give the title compound (10.28 g, 61%); mp 188°-189° after recrystallization from 2-methoxyethanol. Anal. Calcd for C21H18N2O: C, 80.23; H, 5.77; N, 8.91. Found: C, 79.80; H, 5.74; N, 8.87.

Provenance & Evidence