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

HRID 1097106Notes

Reaction equation

HRID 1097106 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>CO.[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)ethanolYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(4-nitro-phenoxy)-ethanol (2.1 g, 12 mmol) in MeOH (30 mL) was flushed with argon and then charged with 10 wt % Pd/C (0.1 equiv by wt). The mixture was evacuated under house vacuum and then refilled with hydrogen from hydrogen balloon. The cycle was repeated again and the mixture stirred at room temperature for 2 h. The heterogeneous reaction mixture was filtered through a pad of Celite, washed with MeOH and concentrated in vacuo to furnish the title compound (1.8 g, 99%) as a brown solid. MS (ES+): m/z 154 (M+H)+.

Workup

  1. customThe mixture was evacuated under house vacuum
  2. additionrefilled with hydrogen from hydrogen balloon
  3. filtrationThe heterogeneous reaction mixture was filtered through a pad of Celite
  4. washwashed with MeOH
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-20a8c42ab0c947e4b992efc9ccb7bc9e
Source dataset
uspto-grants-2012_03
Patent number
US08138199B2

Reaction notes

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