O[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.S(Cl)([Cl:11])=O>C(#N)C>[ClH:11].[Cl:11][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=14-Hydroxymethylpyridine (20) (54.4 g, 0.50 mol) was dissolved in acetonitrile 202 ml. The solution was added dropwise to a mixture of thionyl chloride (65.3 g, 0.55 mol) and acetonitrile (109 ml) under 50° C. The mixture was stirred at the same temperature for 1 hour, then cooled to room temperature to yield a slurry (quantitative) of the objective (21).
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