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

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A solution of 4-methylnicotinonitrile (13.8 g, 0.12 m), dimethylformamide (DMF) (100 mL) and DMF acetal (14.0 g, 0.12 m) was heated at reflux under N2. After 16 hours, the reaction mixture was concentrated at atmospheric pressure until the internal temperature reached 150°. The mixture was then cooled, poured into H2O (1 L) and extracted with C6H6 (6×200 mL). The combined organic extracts were washed with H2O (2×200 mL), dried, filtered and evaporated to dryness. The residue was distilled at 150°-160° (0.2 mm) to yield 12.6 g (63%) of N,N-dimethyl-2-(3-cyano-4-pyridyl)ethenamine. An analytical sample was prepared by crystallization from C6H6 --C6H14, mp 88°-90°.

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