Synthesis and properties of fluorine‐containing heterocyclic compounds. I. trifluoromethyl quinolines

Abstract

Abstract The condensation of ethyl trifluoroacetoacetate with various aromatic amines, in polyphosphoric acid at 150°, gave substituted 2‐trifluoromethyl‐4‐quinolinols. The structure of these compounds was established from a study of their infrared and ultraviolet spectra and, in some cases, by independent synthesis and cyclization of the intermediate 3‐arylaminocrotonates. The 2‐trifluoromethyl‐4‐quinolinols were converted to 2‐trifluoromethyl‐4‐chloroquinolines which were subjected to hydrogenolysis with Raney nickel to yield 2‐trifluoromethylquinolines and to treatment with an excess of hydrazine to give the corresponding hydrazino derivatives. The diazotization of 2 ‐ trifluoromethyl ‐4‐hydrazinoquinolines yielded azides which were unusually stable. The infrared and ultraviolet spectra of some of the compounds prepared are discussed.