Dimethylcarbamoyl Chloride → 4-Methoxypyridine-2-carbonitrile

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Reaction Conditions

Reaction Steps

To a mixture of 4-methoxypiridine-N-oxide (5.00 g, 38.6 mmol) and trimethylsilyl cyanide (4.84 g, 46.3 mmol) in dichloromethane (60 ml) cooled to 0° C. was added dropwise N,N-dimethylcarbamoyl chloride (3.8 ml, 40.5 mmol). The mixture was allowed to warm to ambient temperature and stirred for 16 h. The mixture was cooled to 0° C. and a 30% aqueous solution of K2CO3 (100 ml) was added. The crude product was extracted with dichloromethane (100 ml×2), the organic extracts dried (MgSO4) and evaporated to give 4-methoxy-2-pyridinecarbonitrile (5.35 g, 100%). 1H-NMR (CDCl3) δ: 8.51 (1 H, d, J=5.9 Hz), 7.22 (1 H, d, J=2.6 Hz), 7.01 (1 H, dd, J=2.6, 5.9 Hz), 3.91 (3H, s)

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