3-Nitrophenylethyl alcohol → 2-(3-Aminophenyl)ethan-1-ol

HRID 1419774Notes

Reaction equation

HRID 1419774 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][CH2:8][OH:9])([O-])=O>C(O)C.O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH2:7][CH2:8][OH:9]

Participants

4

Reactant 1

HCID 1040583-Nitrophenylethyl alcohol

Product 1

HCID 149389872-(3-Aminophenyl)ethan-1-olYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-nitrophenethyl alcohol (5.13 g, 30.7 mmol), in ethanol (100 ml), was added a slurry of 10% Pd--C (0.5 g), in water (4 ml), and the mixture hydrogenated in a Parr flask, at 45 psi for 0.75 h. The catalyst was removed by filtration and the solvent evaporated to give 3-aminophenethyl alcohol (4.2 g, 100%), mp 61°-64° C., δ (360 MHz, CDCl3) 2.77 (2H, t, J=6.7 Hz, CH2), 3.80 (2H, t, J=6.7 Hz, CH2), 6.55-6.63 (3H, m, Ar--H), 7.08 (1H, dd, J=7.6 and 8.06 Hz, Ar--H).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-a3f964515ea047778fad5cadf7647bc4
Source dataset
uspto-grants-1999_03
Patent number
US05889008

Reaction notes

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