[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([CH3:21])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.C([O-])=O.[NH4+].ClCCl>[Pd].O>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([CH3:21])[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
A 500 ml round bottomed flask fitted with a teflon stirrer bar was charged with 4-(2-(benzyloxy)ethoxy)-2-methyl-1-nitrobenzene (5.15 g) and methanol (200 ml) and stirred to dissolve all material. The reaction mixture was charged with 10% palladium on charcoal (50% water w/w) and stirred at room temperature. Ammonium formate (20.5 g) was added in one lot and the reaction mixture was stirred at room temperature. After 1 hour, additional ammonium formate (20.5 g) was added, and the progress of the reaction was followed by TLC (silica, dichloromethane). After 4 hours, the reaction was found to be complete. The reaction mixture was then filtered through a plug of Celite, which was washed with methanol (2×50 ml). The resulting filtrate was evaporated under reduced pressure to give a solid. This material was dissolved in water (300 ml), extracted with diethylether (3×100 ml). The combined ethereal solutions were washed with water (2×100 ml) and saturated sodium chloride solution (2×100 ml), dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 4.79 g of 4-(2-(benzyloxy)ethoxy)-2-methylaniline, 1H-NMR (CDCl3) 7.39 (m, 2H), 7.37 (s, 1H), 7.31 (m, 2H), 6.33 (m, 1H), 6.30 (s, 1H), 6.23 (m, 1H), 5.85 (bs, 2H), 4.63 (s, 2H), 4.11 (m, 2H), 3.79 (m, 2H), 2.35 (s, 3H).
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