Phenol, 4-methoxy-2-nitro- → 2-Amino-4-methoxyphenol

HRID 494928Notes

Reaction equation

HRID 494928 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>CO.C(OCC)(=O)C.[C].[Pd]>[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 1

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

Product 1

HCID 14191082-Amino-4-methoxyphenolYield 94.4%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

10 g of 4-methoxy-2-nitrophenol was dissolved in 120 ml of methanol and 80 ml of ethyl acetate. Thereafter, 800 mg of 10% palladium carbon was added to the reaction solution, followed by reduction under hydrogen atmosphere. After completion of the reaction, the catalyst was removed by filtration, and the residue was then concentration under a reduced pressure. The generated solid was suspended in hexane-t-butylmethyl ether, and the suspension was then filtered, so as to obtain 7.77 g of the subject compound.

Workup

  1. customAfter completion of the reaction
  2. customthe catalyst was removed by filtration
  3. concentrationconcentration under a reduced pressure
  4. filtrationthe suspension was then filtered

Sources & evidence

ORD record
ord-6c17ed5b5ccb4ed1b4c57332cd24b93e
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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