Ethanol → (3-Amino-4-(cyclohexylamino)phenyl)methanol

HRID 2068302Notes

Reaction equation

HRID 2068302 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]1

Participants

4

Reactant 2

HCID 702EthanolHCID 46735182(4-(Cyclohexylamino)-3-nitrophenyl)methanol

Product 1

HCID 67254036(3-Amino-4-(cyclohexylamino)phenyl)methanolYield 79%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

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.

Workup

  1. customThe mixture was flushed with hydrogen
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue purified by flash chromatography with a gradient from 40 to 100 percent ethyl acetate in hexanes

Sources & evidence

ORD record
ord-cd68ed013e55493a908052f3d8538884
Source dataset
uspto-grants-2012_10
Patent number
US08293923B2

Reaction notes

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