Sodium Hydroxide → 3-Pyridinecarbonitrile, 2-(chloromethyl)-

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Reaction Steps

165.5 g (0.98 mol) 2-hydroxymethyl-3-pyridinecarboxamide are heated together with 270 ml of phosphorus oxychloride for 1 hour at 90-100° C. The reaction mixture is cooled to ambient temperature and then added dropwise to about 800 ml of water at a temperature of 50-60° C. After hydrolysis of the phosphorus oxychloride the mixture is neutralised while being cooled with sodium hydroxide solution, whereupon the product is precipitated. It is filtered off, washed with 300 ml of water and then dried at 35-40° C.

Provenance & Evidence