2-Methyl-4-methoxy-5-nitrophenol → Phenol, 5-amino-4-methoxy-2-methyl-

HRID 2050751Notes

Reaction equation

HRID 2050751 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-])=O)=[CH:4][C:3]=1[OH:13]>[Pd].C(O)C>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([NH2:10])=[CH:4][C:3]=1[OH:13]

Participants

4

Reactant 1

HCID 199401542-Methyl-4-methoxy-5-nitrophenol

Product 1

HCID 10197787Phenol, 5-amino-4-methoxy-2-methyl-Yield 78.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

320 mg of 10% palladium-on-carbon, 2.90 g (15.8 mmol) of 2-methyl-4-methoxy-5-nitrophenol and 75 ml of ethanol were fed into an autoclave (300 ml). The mixture was then hydrogenated at 50° C. under 50 kg/cm2 for 5 hours. After allowing to cool, the catalyst was filtered off and the solvent was distilled off under reduced pressure. Thus 19.0 g (12.4 mmol) of 2-methyl-4-methoxy-5-aminophenol was obtained in the form of brown crystals. The 1H-NMR spectra of this product showed no impurities. The yield was 78%.

Workup

  1. temperatureto cool
  2. filtrationthe catalyst was filtered off
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-693954398d7e41dea0556f2a066ca45c
Source dataset
uspto-grants-1991_05
Patent number
US05015260

Reaction notes

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