Dimethylformamide → 5-Cyanomethyl-2,6-dimethyl-pyridin-3-yl-acetonitrile

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Reaction Steps

A solution of 3,5-bis-chloromethyl-2,6-dimethyl-pyridine (18.0 g, 88.2 mmol) in dimethylformamide (110 mL, 0.8 M) is cooled to 0° C. and treated with a solution of potassium cyanide (12.4 g, 190 mmol) in water (35 mL). The cooling bath is removed, and after 4 h, ice-cooled H2O (600 mL) is added. The resulting solids are filtered, washed with ice-cooled water (100 mL) and recrystallized from H2O to provide 5-cyanomethyl-2,6-dimethyl-pyridin-3-yl-acetonitrile as light brown flakes (10.9 g, 67%): mp 65-67° C.; Rf 0.23 (20% n-heptane in ethyl acetate); 1H NMR (CDCl3, 300 MHz) δ 7.61 (s, 1 H), 3.69 (s, 4 H), 2.56 (s, 6 H); ESI-LCMS m/z calcd for C11H11N3: 185.1; found 186.0 (M+1)+. Anal. Calcd for C11H11N3.0.15H2O: C, 70.30; H, 6.06; N, 22.36. Found: C, 70.44; H, 6.01; N, 22.13.

Provenance & Evidence