P-Anisidine → HCID 178487932, compound

Participants

Reaction Steps

Ethyl trifluoroacetoacetate and 4-methoxyaniline were reacted together in presence of polyphosphoric acid to give 2-trifluoromethyl-4-hydroxy-6-methoxyquinoline (cf. Jouillie and Dey). The latter was converted to 2-trifluoromethyl-4-chloro-6-methoxy-quinoline by analogy with Example IV. This was in turn converted first to 2-trifluoromethyl-6-methoxyquinoline by hydrogenation in the presence of palladium on charcoal and thence to 2-trifluoromethyl-6-hydroxyquinoline by reaction with aqueous hydrobromic acid. The latter was reacted with (8-bromo-1-tetrahydro pyranyloxy)octane according to Example BIII, 8(2-trifluoromethyl-6-quinolinyloxy)octane-1-ol was prepared and used in Stage b.

Provenance & Evidence