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The unusual reactivity of key enamine intermediates led to the formation of 3-methylamino-2-(2-nitrobenzoyl)-4<i>H</i>-naphthalen-1-one as an unexpected product in an attempted synthesis of the <i>P. aeruginosa</i> metabolite 2-benzyl-4(1<i>H</i>)-quinolone. Although the synthesis of the natural product has not been successful, this methodology allows for the easy preparation of novel derivatives carrying a carboxamide moiety at the C3 position.