Phosphorus oxychloride → 4-Chloro-6-fluoro-2-phenylquinoline

Participants

Reaction Steps

A mixture of 30.4 g (0.127 mol) of 6-fluoro-2-phenyl-4-quinolinol, and 65 ml of phosphorus oxychloride was stirred and heated under reflux for 2 hr. This mixture was concentrated in vacuo, diluted with methylene chloride, and poured onto ice. The aqueous phase was neutralized with 3N sodium hydroxide. The organic phase was separated, and the aqueous phase extracted with methylene chloride. The organic phases were combined, washed with water and with brine, dried over sodium sulfate, and concentrated in vacuo to leave 34.8 g of residue. This was dissolved in methylene chloride, and the solution filtered through a plug of alumina. Concentration of the filtrate left 23.7 g of 4-chloro-6-fluoro-2-phenylquinoline, mp 96°-99°.

Provenance & Evidence