[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([N+:10]([O-])=O)[CH:3]=1.[H][H]>CO.[Pt]>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([CH:3]=1)[NH2:10]To a solution of 4-chloro-2-nitro benzyl alcohol (25.00 g) in methanol (1 ltr) under nitrogen at room temperature, was added platinum on sulfided carbon (2.5 g, 10% by wt). The reaction mixture was shaken under 50 psi of hydrogen until the theoretical uptake of hydrogen had occurred. Filtration, then removal of the solvent in vacuo afforded the desired compound as a solid (21.00 g). δ (360 MHz, DMSO-d6) 4.35 (2H, d, J=4.95 Hz, CH2OH), 5.17 (1H, t, J=4.95 Hz, CH2OH), 6.77 (1H, dd, J=7.98 Hz, J=2.18 Hz, 4-H), 7.06 (1H, d, J=2.18 Hz, 6-H), 7.18 (1H, d, J=7.98 Hz, 3-H), 8.08 (1H, bs, NH2), 8.47 (1H, bs, NH).
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