2-(4-Nitrophenoxy)ethanol → 2-(4-Aminophenoxy)ethanol

HRID 1815902Notes

Reaction equation

HRID 1815902 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:5]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][CH2:10][OH:11])=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 853812-(4-Nitrophenoxy)ethanol

Product 1

HCID 808922-(4-Aminophenoxy)ethanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(4-Nitrophenoxy)ethanol (1.83 g, 10 mmol) was dissolved in EtOH (100 mL) under air at RT. A catalytic amount of 10% Pd/C was added. The air was replaced with a H2(g) atmosphere and the reaction was stirred vigorously for 18 h. The reaction was quenched by filtering it through Celite® with EtOH. The filtrate was concentrated under reduced pressure and the recovered material was purified by eluting it through a 17×2.5 cm column of silica gel (5% and 10% MeOH/CH2Cl2 step gradient) giving 2-(4-amino-phenoxy)ethanol as a black solid: MS m/z 154=[M+H]+. Calc'd for C8H11NO2: 153.08.

Workup

  1. customThe reaction was quenched
  2. filtrationby filtering it through Celite® with EtOH
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe recovered material was purified
  5. washby eluting it through a 17×2.5 cm column of silica gel (5% and 10% MeOH/CH2Cl2 step gradient)

Sources & evidence

ORD record
ord-a853cbe5c85441348edc5da81b5f4447
Source dataset
uspto-grants-2005_04
Patent number
US06881737B2

Reaction notes

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