Dimethylcarbamoyl Chloride → 4-Methoxypyridine-2-carbonitrile

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Reaction Steps

To a stirring mixture of 1.2 g (9.67 mmol) of 4-methoxypyridine-N-oxide in 18 mL of CH2Cl2 at r.t. was added 1.6 mL (12.0 mmol) of TMSCN. After 5 min. 0.9 mL (9.8 mmol) of dimethylcarbamoyl chloride. The solution was stirred at r.t. for 13 h and CHCl3 and 20 mL of 10% K2CO3 was added. The aqueous layer was extracted with CHCl3 3 times, and the combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (38-44% EtOAc/hexanes) provided 949 mg of 4-methoxypicolinonitrile as a colorless solid in 73% yield.

Provenance & Evidence