[CH3:1][O:2][C:3]1[C:17]([N+:18]([O-])=O)=[CH:16][C:6]2[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][O:14][CH3:15])[CH2:10][CH2:11][C:5]=2[CH:4]=1.O.NN>[Pd].CO>[CH3:1][O:2][C:3]1[C:17]([NH2:18])=[CH:16][C:6]2[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][O:14][CH3:15])[CH2:10][CH2:11][C:5]=2[CH:4]=1Into a 1-neck round-bottom flask was added 7-methoxy-3-(2-methoxy-ethyl)-8-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine (2.4 g, 8.56 mmol), hydrazine monohydrate (20 mL, 0.4 mol), and palladium on carbon (10% wt, 50% wet; 400 mg), in methanol (80 mL). The reaction mixture was heated at 70° C. for 3 hours. The reaction mixture was filtered through Celite and was concentrated. The residue was partitioned between diluted NaHCO3 and ethyl acetate. The aqueous phase was extracted with another portion of ethyl acetate, dried (MgSO4), and concentrated to afford 8-methoxy-3-(2-methoxy-ethyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamine (2.00 g, 93%). 1H-NMR (CDCl3) δ 6.55 (s, 1H), 6.49 (s, 1H), 3.81 (s, 3H), 3.63 (br s, 2H), 3.53 (t, J=5.8 Hz, 2H), 3.36 (s, 3H), 2.60-2.90 (m, 10H); LC/MS (ESI+): 251.10 (M+H).
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