1-(4-Methylphenyl)-2-nitroethanol → 2-Amino-1-(4-methylphenyl)ethan-1-ol

HRID 1994469

Reaction equation

HRID 1994469 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[CH2:9][N+:10]([O-])=O)=[CH:4][CH:3]=1>CCO.[Pd]>[NH2:10][CH2:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[OH:13]

Participants

4

Reactant 1

HCID 114808201-(4-Methylphenyl)-2-nitroethanol

Product 1

HCID 35199292-Amino-1-(4-methylphenyl)ethan-1-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 10% Pd/C (24 mg) in a solution of 1-(4-methylphenyl)-2-nitroethanol (50 mg, 0.276 mmol) in absolute EtOH (1 mL) was stirred overnight at room temperature under 15 psi of H2. The reaction mixture was filtered through a pad of Celite and the filtrate was concentrated in vacuo to afford 2-amino-1-(4-methylphenyl)ethanol as an oil. LCMS calc.=152.10; found=152 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.20 (d, J=8.0 Hz, 2H), 7.13 (d, J=8.0 Hz, 2H), 4.57 (dd, J=7.9, 3.9 Hz, 1H), 2.86 (dd, J=12.7, 3.9 Hz, 1H), 2.76 (dd, J=12.7, 7.9 Hz, 1H), 2.33 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7ac50567804345c6ad2ceba52cf52f92
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Linked notes

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