[CH3:1][C:2]1([CH3:17])[C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-])=O)=[CH:12][C:7]=2[CH2:6][CH2:5][C:4](=[O:16])[NH:3]1.[O-]S(S([O-])=O)=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[Na+].[Cl-]>C1COCC1.CO.O.CCOC(C)=O>[NH2:13][C:11]1[CH:10]=[CH:9][C:8]2[C:2]([CH3:17])([CH3:1])[NH:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]=2[CH:12]=1A solution of 1,1-dimethyl-7-nitro-1,2,4,5-tetrahydrobenzo[c]azepin-3-one (1.75 g) in THF (175 mL) and MeOH (20 mL) was treated with an solution of Na2S2O4 (5 g) and sodium bicarbonate (5 g) in water (200 mL). After 15 minutes, 250 mL of EtOAc and 250 mL saturated NaCl was added and the organic layer was separated. The aqueous layer was extracted again with EtOAc and the combined organic layers were washed again with brine. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo to provide 400 mg of 7-amino-1,1-dimethyl-1,2,4,5-tetrahydrobenzo[c]azepin-3-one: 1H NMR (300 MHz, CDCl3) δ 7.1 (d, 1H, C9-H), 6.5 (dd, 1H, C8-H), 6.4 (d, 1H, C6-H), 3.0 (m, 2H), 2.6 (m, 2H), 1.6 (s, 6H).
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