Dimethylformamide → 8-Amino-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one

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A solution of 8-nitro-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one (0.23 g, 0.00096 mol), 10% palladium on carbon (0.02 g), DMF (10 mL), and ethanol (30 mL) was hydrogenated for 3 days. Filtration and evaporation gave an oil which was chromatographed on Al2O3 to give 8-amino-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one (0.06 g, 35%) as a tan solid. MP: 151-2° C.; 1H-NMR (DMSO-d6) δ 7.77 (s, 1H), 7.54-6 (d, 1H), 6.25-7 (d, 1H), 6.05 (s, 1H), 5.63 (s, 2H), 4.17-9 (m, 2H), 3.25-8 (m, 2H); LC/MS (ESI+): 179 (M+H).

Provenance & Evidence