3-Cyano-2,6-dichloro-4-methylpyridine → (E)-2,6-Dichloro-4-(2-(dimethylamino)vinyl)nicotinonitrile

Participants

Reaction Conditions

Reaction Steps

To 2,6-dichloro-4-methylnicotinonitrile (20.3 g, 0.108 mol) in 200 mL of isopropyl alcohol is added N,N-dimethylformamide dimethylacetal (14.4 mL, 0.108 mol) and the reaction is stirred at 65° C. for 18 hrs. After the reaction is cooled to ambient temperature, the precipitate is collected by filtration, washed with 50 mL of isopropyl alcohol, and air dried giving (E)-2,6-Dichloro-4-(2-(dimethylamino)vinyl)nicotinonitrile as a yellow solid. MS (ES+) calcd. 242.02. found 242.10 (MH+). H-NMR (600 MHz, DMSO-d6) 2.90 (br.s, 3H), 3.17 (br.s, 3H), 5.05 (d, J=12.6 Hz, 1H), 7.61 (s, 1H), 8.09 (d, J=12.6 Hz, 1H).

Provenance & Evidence