Ethanol → 2-Amino-4-methoxyphenol

HRID 2077221Notes

Reaction equation

HRID 2077221 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([N+:10]([O-])=O)[CH:4]=1.C(O)C>[Pd].C(OCC)(=O)C>[NH2:10][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[OH:9]

Participants

5

Reactant 2

HCID 702EthanolHCID 15285Phenol, 4-methoxy-2-nitro-

Product 1

HCID 14191082-Amino-4-methoxyphenolYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-methoxy-2-nitrophenol (30.2 g, 0.18 mol), 10% Pd/C, ethanol (200 mL), and ethyl acetate (200 mL) was hydrogenated at ambient pressure and temperature for three days before it was filtered and concentrated in vacuo to give the title compound as a dark brown solid (20.78 g): 1H NMR (CDCl3, 200 MHz): δ=6.64 (m, 1H), 6.32 (m, 1H), 6.21 (m, 1H), 3.71 (s, 3H).

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f83f64114c76447ba00dd58d8a3aa5c9
Source dataset
uspto-grants-2011_04
Patent number
US07928120B2

Reaction notes

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