Hydrochloric Acid → HCID 69213011, compound

Participants

Reaction Steps

To a stirred solution of 1-(2-aminophenyl)-ethanone (8.00 g, 59.20 mmol) in THF (200 mL) at 0° C. was slowly added 4-chlorophenyl magnesium bromide (1.0 M, 178 mL, 178 mmol) in ether. The reaction was allowed to warm to room temperature. After 3 hours, the reaction mixture was quenched with ammonium chloride solution (sat.) and extracted several times with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated. The crude solid was taken up in THF (200 mL) and CDI (10.56 g, 65.10 mmol) was added. The reaction solution was stirred overnight at room temperature, poured into 1N HCl, and extracted several times with ethyl acetate. The combined organic layers were dried over magnesium sulfate and trituration with ether gave 4-(4-chlorophenyl)-4-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one as a tan solid (5.19 g, 32%). 1H NMR (DMSO-d6): δ 10.30 (s, 1H), 7.46 (m, 3H), 7.36 (td, J=7.7, 1.0 Hz, 1H), 7.25 (d, J=8.6 Hz, 2H), 7.15 (t, J=7.6 Hz, 1H), 6.92 (d, J=7.7 Hz, 1H), 1.94 (s, 3H); MS (ESI) m/z [M+H]+=(274/276); MS (ESI) m/z [M−H]−=(272/274); Anal. calcd for C15H12ClNO2: C, 65.82; H, 4.42; N, 5.12. Found: C, 65.38; H, 4.58; N, 5.00.

Provenance & Evidence