[C:1]([C:5]1[C:13]([N+:14]([O-])=O)=[CH:12][C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.C(O)C>[Fe].O>[C:1]([C:5]1[C:13]([NH2:14])=[CH:12][C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]The above prepared 5-tert-Butyl-6-nitrobenzo[d][1,3]dioxole (1.1 g, 5 mmol), Fe (5.5 g, 100 mmol) and HCl (2 ml) was added into ethanol (6 ml) and water (18 ml). The mixture was stirred for 2 h at refluxed temperature. The PH was adjusted to 7-8 and the mixture was filtered and washed with methanol. The filtrate was concentrated and purified by column chromatography (petroleum ether/ethyl acetate 1%-5%) to give 6-tert-butylbenzo[d][1,3]dioxol-5-amine (240 mg, 25%) as a red solid. LCMS: 194 [M+1]+; 1H NMR (400M): (DMSO-d6) δ 1.28 (s, 9H), 4.46 (s, 2H), 5.77 (s, 2H), 6.32 (s, 1H), 6.63 (s, 1H).
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