6-methoxypyridine-2-carbonitrile

Synthesis

98276-69-8

83621-01-6

GENERAL STEPS: To a solution of 6-methoxypyridine-2-carboxamide (300 mg, 1.97 mmol) in tetrahydrofuran (THF, 3 mL) was added triethylamine (1.25 mL, 8.68 mmol), followed by the slow dropwise addition of trifluoroacetic anhydride (TFAA, 0.61 mL, 4.34 mmol), under ice-bath conditions. The reaction mixture was gradually warmed to room temperature and stirred overnight. Upon completion of the reaction, the volatile solvent was removed by distillation under reduced pressure and the remaining liquid residue was slowly added dropwise to vigorously stirred, ice-cold pH 7 phosphate buffer solution (5 mL). After continued stirring for 15 min, the resulting pale yellow solid was collected by filtration and dried in air for 1 h. 6-Methoxypyridine-2-carbonitrile (250 mg, 95% yield) was obtained as a pale yellow solid with a mass spectrum (m/z): 135.4 [M + 1]+.

References