Dimethylformamide dimethyl acetal → 4-[2-(Dimethylamino)ethenyl]pyridine-3-carbonitrile

Participants

Reaction Steps

A solution of 3-cyano-4-methylpyridine (25 g, 0.21 mol), and N,N-dimethylformamide dimethyl acetal (29.2 mL, 0.22 mol) in dry DMF was heated at reflux overnight. Most of the DMF was removed under reduced pressure. The crude red oil was partitioned between EtOAc (300 mL) and H2O (300 mL) and the organic phase was washed with H2O, brine and dried (Na2SO4). Removal of the solvent afforded the product (34.3 g, 94%, as a light red solid of suitable purity for use directly in the next step, mp 80°-83° C.). An analytical sample was prepared by recrystallizing a sample of the crude product from benzene/petroleum ether, (mp 88°-89° C., light red solid).

Provenance & Evidence