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

HRID 2067864Notes

Reaction equation

HRID 2067864 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 8 (109 mmol) and Pd/C (10% wt.) are suspended in EtOH (50 mL) and allowed to absorb 30 psi of hydrogen in a Parr shaker. The mixture is shaken at rt for 16 h. After filtration and concentration, 2-(4-aminophenoxy)ethanol 9 is obtained as a light pink colored solid and used in the next step without purification. MS (m/z) (M+1)+: 154.1.

Workup

  1. customto absorb 30 psi of hydrogen in a Parr shaker
  2. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-6799483bc7a74c61958f276ef2fc190d
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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