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

HRID 1482669Notes

Reaction equation

HRID 1482669 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 79.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of Pd/C (0.27 g) in methanol (27 mL), 2-(4-nitrophenoxy)ethanol (2.70 g) was added under nitrogen atmosphere into the 50 mL 3-neck RBF at room temperature. Hydrogen gas was bubbled for 1-2 hr at room temperature. The reaction was monitored on TLC using chloroform:methanol (9.8:0.2) as mobile phase. After completion, the reaction mixture was filtered using Celite and washed with methanol. The filtrate was concentrated under reduced pressure at 40° C. to give 1.8 g of 2-(4-aminophenoxy)ethanol as a dark brown liquid.

Workup

  1. additionwas added under nitrogen atmosphere into the 50 mL 3-neck RBF at room temperature
  2. customHydrogen gas was bubbled for 1-2 hr at room temperature
  3. filtrationAfter completion, the reaction mixture was filtered
  4. washwashed with methanol
  5. concentrationThe filtrate was concentrated under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-3c342156f14746a497abc1852f7a4029
Source dataset
uspto-grants-2016_08
Patent number
US09415049B2

Reaction notes

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