Phosphorus oxychloride → HCID 178426119, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,4-dihydroxy-6-methylnicotinonitrile (1.5 g, 10 mmol) in acetonitrile (50 mL) were added benzyltriethylammonium chloride (9.1 g, 40 mmol) and phosphoryl chloride (6.13 g, 40 mmol). The reaction mixture was heated to 40° C. for 4 hours at the same temperature. LC-MS showed that 2,4-dihydroxy-6-methylnicotinonitrile was consumed completely. The solvent was removed by rotary evaporation. To the residue was added dichloromethane (100 ml) and water (50 ml). The organic phase was separated, and it was washed with brine (50 ml) once, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give crude product which was purified by silica gel column chromatography with dichloromethane/methanol=10:1 to afford 4-chloro-2-hydroxy-6-methylnicotinonitrile (800 mg, 24% yield) as a brown solid.

Provenance & Evidence