2-Propenoic acid, 3-phenyl- → HCID 131722398, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,5-dimethoxy aniline 1 (10.3 g, 67.5 mmol) and potassium carbonate (13.9 g, 101.2 mmol) was taken in acetone-water (150 mL, 1:2) and cooled to 5° C. Cinnamoyl chloride (12.2 g, 67.5 mmol) (prepared by treatment of a solution of cinnamic acid (10 g, 67.5 mmol) in benzene (40 mL) with thionyl chloride (8 g, 67.5 mmol) at reflux temperature for 1 h.) was added in 15 min. to reaction mixture while maintaining temperature below 5° C. Reaction mixture was stirred below 5° C. for 30 min. and allowed to raise to room temperature over a period of 30 min. (TLC, hexane:ethyl acetate, 7:3, Rf=0.4). The reaction mixture was diluted with water (100 mL) and solid separated was filtered. The solid was washed with water (2×50 ml) dried under vacuum to afford 1N-(3,5-dimethoxyphenyl)-3-phenyl-(E)-2-propenamide (2) (18.1 g) in 95% yield as a off white solid. M.P. 142-145° C.

Provenance & Evidence