3-(Trifluoromethyl)aniline → 3-Phenylquinazolinone

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A mixture of 2-methyl-4H-Benzo[d][1,3]oxazin-4-one (12; 1.0 g, 6.2 mmol) and 3-trifluoromethylaniline (13, R═H, 0.77 mL, 6.2 mmol, 1.0 eq) were heated at 160° C. (oil bath) for 12 hours. The reaction was cooled to room temperature and the resulting solid was subjected to chromatography on silica gel with 20-50% EtOAc/hexane. Product-containing fractions were pooled and evaporated to yield 1.08 g mg (56%) of 14 as a yellow solid: 1H NMR (CDCl3): 8.27 (d, 1H), 7.29-7.28 (m, 7H), 2.25 (s, 3H).

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