[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([O:12][CH3:13])=[CH:5][C:4]=1[O:14][CH3:15].O.O.[Sn](Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:13][O:12][C:6]1[CH:5]=[C:4]([O:14][CH3:15])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[NH2:9]1,2,4-Trimethoxy-5-nitro-benzene (1.20 g, 5.63 mmol) and tin chloride dihydrate (3.81 g, 16.9 mmol) in ethyl acetate (50 mL) was stirred at 65-70° C. for 20 h. The reaction was cooled, carefully neutralized with sodium bicarbonate and was filtered through Celite. The organic phase was washed with brine, dried (sodium sulfate) and was evaporated. Purification by flash chromatography (SiO2) eluted with 3:7 ethyl acetate:hexanes provided 2,4,5-trimethoxy-phenylamine (0.56 g, 54% yield) as a tan solid. 1H-NMR (DMSO-d6, 500 MHz) 6.57 (s, 1H), 6.37 (s, 1H), 3.70 (s, 3H), 3.65 (s, 3H), 3.63 (s, 3H) ppm; HPLC (Method A) 2.163 min.
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