Hydrazine hydrate (1:1) → 7-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

반응식

O.NN.[CH3:4][C:5]1([CH3:20])[CH2:11][CH2:10][C:9](=[O:12])[NH:8][C:7]2[CH:13]=[CH:14][C:15]([N+:17]([O-])=O)=[CH:16][C:6]1=2>[Pd].C(O)C>[NH2:17][C:15]1[CH:14]=[CH:13][C:7]2[NH:8][C:9](=[O:12])[CH2:10][CH2:11][C:5]([CH3:20])([CH3:4])[C:6]=2[CH:16]=1

참가 물질

실험 절차

Added 13 mL of ethanol, 10% Palladium on activated carbon (62 mg), and hydrazine monohydrate (171 ul) to 5,5-Dimethyl-7-nitro-1,3,4,5-tetrahydrobenzo[b]azepin-2-one (206 mg, 0.8793 mmol). Heated reaction to 60° C. overnight. Filtered reaction through Celite, and purified by normal phase silica gel chromatography eluting with 90/10/1 CH2Cl2/MeOH/NH4OH to obtain an off-white solid to yield 7-Amino-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one. mp 168° C.; LCMS: m/z=205.12 (M+H+), 1H NMR (400 MHz, CDCl3) δ 8.35 (br s, 1H), 6.78 (d, 1H, J=8.3 Hz), 6.72 (s, 1H), 6.54 (d, 1H, J=8.3 Hz), 3.76 (br s, 2H), 2.32 (m, 2H), 2.06 (m, 2H), 1.35 (s, 6H).