Ethanol → (3-Amino-4-(cyclohexylamino)phenyl)methanol
Reaction equation
[CH:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][C:9]=2[N+:16]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C>[Pd]>[NH2:16][C:9]1[CH:10]=[C:11]([CH2:14][OH:15])[CH:12]=[CH:13][C:8]=1[NH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To (4-cyclohexylamino-3-nitro-phenyl)methanol (1.46 g, 0.0058 mol) in ethanol (35 mL, 0.6 mol) was added 5% Pd/C (0.20 g, 0.00009 mol). The mixture was flushed with hydrogen then stirred for 2 hr at room temperature under 1 atm of hydrogen. The reaction mixture was concentrated and the residue purified by flash chromatography with a gradient from 40 to 100 percent ethyl acetate in hexanes to provide 1.010 g the title compound.