Thionyl Chloride → 4-(Chloromethyl)picolinonitrile hydrochloride

Participants

Reaction Steps

A mixture of 2-cyano-4-hydroxymethylpyridine (0.51 g, 3.8 mmol)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%). 1H NMR Spectrum: (DMSOd6) 4.75(s, 2H); 7.75(dd, 1H); 8.05(s, 1H); 8.34(d, 1H)

Provenance & Evidence