Hydrochloric Acid → Methyl-(3,4-dimethoxy)-cinnamoimidate hydrochloride

Participants

Reaction Steps

A suspension of 3,4-dimethoxycinnamonitrile (10 g; 52 mmol) in EtOH (150 mL) was cooled in an ice bath. The cold mixture was then saturated with hydrogen chloride. The reaction solution was refrigerated for 18 hours. The precipitate formed was collected by filtration. The colorless solid gave 8.0 g (60% yield) of methyl-(3,4-dimethoxy)-cinnamoimidate hydrochloride which was used in the next reaction, 1H-NMR (DMSO-d6; 200 MHz) δ11.8 (broad s, 1H), 10.9 (broad s, 1H), 7.82-7.9 (d, 1H), 7.3 (d, 2H), 7.02-7.12 (d, 1H), 6.81-6.9 (d, 1H), 4.2 (s, 3H), and 3.76 (s, 3H), 3.82 ppm (s, 3H).

Provenance & Evidence