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 aniline (13, R═H, 0.57 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 recrystallized from EtOH to yield 485 mg (31%) of 14 as a yellow-orange crystalline solid: 1H NMR (CDCl3): 8.28 (d, 1H), 7.80-7.67 (m, 2H), 7.60-7.44 (m, 4H), 7.29-7.28 (m, 2H), 2.25 (s, 3H).

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