Malononitrile → 2-Amino-5-(4-chlorophenyl)pyridine-3-carbonitrile

Participants

Reaction Steps

Sodium methoxide (16.2 grams) in 300 ml methanol and malononitrile (19.8 grams) in 50-100 ml methanol were added to N-[2-(4-chlorophenyl)-3-(dimethylamino)-2-propenylidene]-N-methylmethanaminium perchlorate (101.1 grams) in 300 ml pyridine at 0° C. in an ice-alcohol bath. The reaction mixture was stirred at room temperature for about 20 hours and then recooled to 0° C. Ammonium hydroxide (120 ml) was added and after three hours, a copious precipitate formed. The solid was filtered, washed with water, and shown by NMR to be the desired product, yield 44 grams, m.p. 202°-204° C. Addition of 600-800 ml of water to the filtrate gave additional product although impurities were present.

Provenance & Evidence