Dimethylcarbamoyl Chloride → 6-Cyanopyridine-3-carboxylic acid

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Reaction Steps

To a suspension of nicotinic acid N-oxide (0.7 g, 5 mmol) in 10 ml of dichloromethane is added trimethylsilylcyanide (0.55 g, 5,5 mmol), and the solution is stirred for 5 min. Then dimethylcarbamoyl chloride (0.54 g, 5 mmol) is added, and stirring is continued for 5 days under reflux. After cooling, the solution is evaporated to dryness under reduced pressure, and the residue is dissolved in 50 ml of hot water. After standing overnight, the white precipitate is filtered off and is purified by column chromatography (ethyl acetate/ethanol 1:1) to yield 5-carboxy-2-cyano-pyridine, m.p. 194°-195° C., Rf =0.54.

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