Aniline → HCID 178516126, compound

Participants

Reaction Steps

Aniline (ex Aldrich) and ethyl trifluoroacetoacetate (ex Lancaster) were reacted together according to Westland et al, J. Med. Chem., 16, 326 (1973), to give 2-hydroxy-4-trifluoromethylquinoline. The latter (2.5 g), was treated for 30 minutes at 90°-100° C. with phosphorous oxychloride (20 ml) and resublimed phosphorous pentachloride (2.45 g). The reaction mixture was allowed to cool and poured onto ice-water and neutralised with aqueous ammonium hydroxide. Extraction into diethyl ether yielded 2-chloro-4-trifluoromethyl quinoline, which after conventional work-up was used directly in Stage a.

Provenance & Evidence