C(O)C.O.NN.[CH2:7]([N:9]1[C:15](=[O:16])[CH2:14][CH2:13][C:12]([CH3:18])([CH3:17])[C:11]2[CH:19]=[C:20]([N+:23]([O-])=O)[CH:21]=[CH:22][C:10]1=2)[CH3:8]>[Pd].O>[NH2:23][C:20]1[CH:21]=[CH:22][C:10]2[N:9]([CH2:7][CH3:8])[C:15](=[O:16])[CH2:14][CH2:13][C:12]([CH3:17])([CH3:18])[C:11]=2[CH:19]=1Added 30 mL of ethanol, 10% Palladium on activated carbon, 50% wet with water for safety (273 mg), and hydrazine monohydrate (400 ul) to 1-Ethyl-5,5-dimethyl-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (537 mg, 2.047 mmol). Heated reaction to 60° C. for 24 hours. Filtered reaction through Celite, and concentrated under reduced pressure. Purified with normal phase silica gel chromatography eluting with 40% to 60% ethyl acetate in hexane to obtain a yellow sticky solid, 7-Amino-1-ethyl-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (347 mg, 73%). LCMS: m/z=233.07 (M+H+), 1H NMR (400 MHz, DMSO-d6) δ 6.98 (d, 1H, J=8.9 Hz), 6.59 (d, 1H, J=1.8 Hz), 6.48 (dd, 1H, J=8.3, 1.5 Hz), 5.08 (s, 2H), 3.58 (m, 2H), 1.96 (m, 4H), 1.17 (m, 9H).
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