[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:4]=1[CH2:5][OH:6].Cl[Sn]Cl.O.[OH-].[Na+]>CCO>[OH:6][CH2:5][C:4]1[CH:7]=[C:8]([CH:9]=[CH:10][C:3]=1[O:2][CH3:1])[NH2:11].[NH2:11][C:8]1[CH:9]=[CH:10][CH:3]=[CH:4][CH:7]=1A mixture of 2-methoxy-5-nitrobenzylalcohol (1.02 g, 6.03 mmol) and SnCl2.H2O (6.8 g, 30.15 mmol) in EtOH (20 mL) was heated at 70° C. for 1 hour. After cooling, the mixture was treated with 2M NaOH and extracted with ether. The organic layer was washed with water, dried, and evaporated under vacuum to provide 2.18 g (84%) of the aniline 3-hydroxymethyl-4-methoxyaniline: 1H NMR (DMSO-d6, 500 MHz) δ 6.66 (d, 1H, J=2.2 Hz), 6.61 (d, 1H, J=8.6 Hz), 6.38 (dd, 1H, J=2.4 and 8.2 Hz), 4.81 (t, 1H, J=5.5 Hz), 4.54 (br, 2H), 4.37 (d, 2H, J=5.8 Hz), 3.61 (s, 3H).
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