[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:7]=2[NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH2:3][CH2:2]1.[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:12][C:10]1[CH:9]=[CH:8][C:7]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[C:6]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)[CH:11]=1A mixture of N-(2-(cyclopropylmethoxy)-4-nitrophenyl)methanesulfonamide (0.830 g, 2.90 mmol), iron (0.971 g, 17.39 mmol), and NH4Cl (0.099 g, 1.848 mmol) in EtOH (15 ml) and water (6 ml) was heated to reflux for 30 minutes. The hot reaction mixture was filtered and the filtrate was evaporated. The residue was portioned between EtOAc and water; the organic phase was washed with brine and dried over Na2SO4. The solvent was removed affording N-(4-amino-2-(cyclopropylmethoxy)phenyl)-methanesulfonamide (0.679 g, 2.65 mmol, 91% yield, MS/ESI+ 256.9 [MH]+).
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