3,4-Dimethoxyaniline → 2-Cyano-3-(3,4-dimethoxyphenylamino)acrylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

3,4-dimethoxyaniline (30.6 g, 200 mmol) was diluted with toluene (80 mL) and to the resultant solution was added ethyl(ethoxymethylene)cyanoacetate (33.8 g, 200 mmol). The resultant reaction was heated to 100° C. and allowed to stir at for 1 hour, then heated to 125° C. and allowed to stir for 15 minutes. The reaction mixture was cooled to room temperature and concentrated in vacuo to provide a crude residue, which was recrystallized from EtOAc to provide 2-cyano-3-(3,4-dimethoxyphenylamino)acrylic acid ethyl ester as a tan solid (40.0 g, 72%). mp 166-170° C.; MS (ES+) m/z 277.2 [M+H].

Provenance & Evidence