Ethanol → 2-Amino-4-methoxyphenol

HRID 409296Notes

Reaction equation

HRID 409296 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-3db219a25e6f456ea8aa26dbfdb03fb9
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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