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1H NMR Spectrum: (DMSOd6) 4.65(s, 2H); 5.70(t, 1H); 7.70(d, 1H); 7.95(s, 1H); 8.75(d, 1H) A mixture of 2-cyano-4-hydroxymethylpyridine (0.51 g, 3.8mmol) and thionyl chloride (0.6 ml) in toluene (20 ml) was stirred at room temperature for 1 hour. The volatiles were removed by evaporation and the residue azeotroped with toluene to give 4-chloromethyl-2-cyanopyridine hydrochloride (620 mg, 86%).

1. customThe volatiles were removed by evaporation
2. customthe residue azeotroped with toluene