1-methyl-7-nitro-4,5-dihydro-3,1-benzoxazepin-2(1H)-one → 7-amino-1-methyl-4,5-dihydro-3,1-benzoxazepin-2(1H)-one

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Reaction Steps

A mixture of 2-nitro-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one (0.7 g) and 50% Raney Ni (1 mL) in ethanol (25 mL) was hydrogenated at 30 psi for 3 hours. The reaction mixture was filtered through celite and concentrated to yield 2-amino-5-methyl-8,9-dihydro-5H-7-oxa-5-aza-benzocyclohepten-6-one: 1H NMR (300 MHz, CDCl3) δ 6.94 (d, 1H), 6.60 (dd, 1H), 6.53 (d, 1H), 4.45 (t, 2H), 3.67 (bs, 1H), 3.33 (s, 3H), 2.87 (t, 2H).

Provenance & Evidence