Thionyl Chloride → 5-(Chloromethyl)pyridine-3-carbonitrile

Participants

Reaction Steps

Add thionyl chloride (1 mL) to a solution of 5-hydroxymethyl-nicotinonitrile (45 mg, 0.34 mmol, 1 equiv) in anhydr CH2Cl2 (1 mL). After 20 min, basify the reaction with satd aq NaHCO3 (12 mL). Extract this mixture with Et2O (2×5 mL). Dry the combined organic layers (anhydr MgSO4) and rotary evaporate (40° C.) to yield 4.9 mg (9.6%) of 5-chloromethyl-nicotinonitrile as a yellow film. MS (m/z): 152.

Provenance & Evidence