Diethyl Ether → 6-Chloro-4-methylpyridine-2-carbonitrile

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Reaction Steps

2-chloro-4-methylpyridine 1-oxide (8.5 g, 59.2 mmol) from step 1 of this example was added to the dimethyl sulfate (9.0 g, 71 mmol) and the mixture stirred overnight. Diethyl ether (40 ml) was added, the mixture stirred, and ether decanted (2×). The volatiles were removed in vacuum. The residue was dissolved in water (50 ml) and the solution added drop wise to a −15° C. solution of sodium cyanide (11.3 g, 231 mmol) in water (50 ml) under N2. The mixture was stirred between −7 and −15° C. for 1.5 hours during which a solid precipitates. The crystals were filtered, washed with water followed by a small amount of cold ether to give the titled compound. LRMS calc: 152.01; obs: 153.56 (M+1).

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