Keywords: Ethyl trifluoroacetoacetate / Halogen/metal permutations / Hydrogen/metal permutations / KnorrϪConradϪLimpach cyclizations / NMR spectroscopy Under carefully controlled conditions, ethyl 4,4,4-trifluoroacetoacetate (ethyl 4,4,4-trifluoro-3-oxobutanoate) can be condensed with anilines and subsequently cyclized to give 4-trifluoromethyl-2-quinolinones 1 although only in poor yield. Heating these products with phosphoryl tribromide affords 2-bromo-4-(trifluoromethyl)quinolines 2 which can be converted into 4-(trifluoromethyl)quinolines 3 by reduction, 4-trifluoromethyl-2-quinolinecarboxylic acids 4 by permutational halogen/metal exchange followed by carboxylation,''To kill two birds with one stone'' is a saying that finds its chemical equivalent in the conversion of the same starting material into two different products. An early example was published more than a century ago by R. Knorr.[1] Aniline and ethyl acetoacetate react with each other at ambient temperature to form an imino ester (in equilibrium with the tautomerically predominent ethyl 3-anilino-2-butenoate) which gives 4-quinolinone upon acid-catalyzed cyclization [1] whereas the acetoacetanilide (or the tautomeric enol) and, after acid treatment, the 2-quinolinone are obtained when the condensation between aniline and the dicarbonyl compound is carried out at temperatures around 150°C. and 2-bromo-4-trifluoromethyl-3-quinolinecarboxylic acids 5 by consecutive treatment with lithium diisopropylamide and dry ice. Debromination of acids 5 makes 4-trifluoromethyl-3-quinolinecarboxylic acids 6 available. As at any time 2-trifluoromethyl-4-quinolinones 9 may form instead of the expected isomers 1, the structures have to be assigned on the basis of unequivocal NMR spectral criteria.