Phosphorus oxychloride → (6-Chloropyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

69.5 g (0.5 mol) of 6-hydroxynicotinic acid are introduced into a mixture of 200 g (1 mol) of phosphorus pentachloride and 233 g (1.5 mol) of phosphorus oxychloride at room temperature, the mixture is stirred at 95° C. for 5 hours and excess phosphorus chlorides are then removed in vacuo. The crystalline residue is introduced into a solution of 75 g (1.98 mol) of sodium borohydride in 1,000 ml of water, the temperature being maintained at 30° C. at most. The mixture is then stirred at room temperature until the completion of gas evolution and is filtered with suction from solid material, and the filtrate is extracted using ether.

Provenance & Evidence