O.NN.[CH3:4][C:5]1([CH3:19])[CH2:11][CH2:10][CH2:9][NH:8][C:7]2[CH:12]=[CH:13][C:14]([N+:16]([O-])=O)=[CH:15][C:6]1=2>[Pd].C(O)C>[CH3:4][C:5]1([CH3:19])[CH2:11][CH2:10][CH2:9][NH:8][C:7]2[CH:12]=[CH:13][C:14]([NH2:16])=[CH:15][C:6]1=2Added 6 mL of ethanol, 10% Palladium on activated carbon (50% wet with water for safety) (60 mg), and hydrazine monohydrate (89 ul) to 5,5-Dimethyl-7-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine (101 mg, 0.459 mmol). Heated reaction to 60° C. for 22 hours. Filtered reaction through Celite, and concentrated under reduced pressure. Purified with normal phase silica gel chromatography eluting with 5% methylene chloride in methanol to obtain a brown oil, 5,5-Dimethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-7-ylamine (79 mg, 91%). LCMS: m/z=190.99 (M+H+), 1H NMR (400 MHz, CDCl3) δ 6.73 (d, 1H, J=2.0 Hz), 6.55 (d, 1H, J=8.1 Hz), 6.43 (dd, 1H, J=8.1, 1.5 Hz), 3.40 (br s, 3H), 2.97 (m, 2H), 1.86 (m, 2H), 1.59 (m, 2H), 1.38 (s, 6H).
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