2-(3-Methyl-4-nitrophenoxy)ethanol → 2-(4-Amino-3-methylphenoxy)ethan-1-ol

HRID 402639Notes

Reaction equation

HRID 402639 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-])=O)[O:5][CH2:6][CH2:7][OH:8]>CO.O1CCCC1.[Pd]>[OH:8][CH2:7][CH2:6][O:5][C:4]1[CH:9]=[CH:10][C:11]([NH2:12])=[C:2]([CH3:1])[CH:3]=1

Participants

4

Reactant 1

HCID 100585272-(3-Methyl-4-nitrophenoxy)ethanol

Product 1

HCID 4592592-(4-Amino-3-methylphenoxy)ethan-1-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 2-(3-methyl-4-nitrophenoxy)ethanol (1.0 g, 5.3 mmol) was dissolved in methanol/tetrahydrofuran (30 mL/30 mL) and 10% palladium on carbon (0.37 g) was added at ambient temperature. The reaction mixture was agitated under a hydrogen atmosphere for 4 h. Palladium on carbon was removed by filtration with Celite and the solvent was removed under reduced pressure to afford 4-(2-hydroxyethoxy)-2-methylaniline as solid (0.80 g, y. 90%).

Workup

  1. customPalladium on carbon was removed by filtration with Celite
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0889592fcfef4dc9abcf539cfbb90192
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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