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

HRID 1031657Notes

Reaction equation

HRID 1031657 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.[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

4

Reactant 1

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

Product 1

HCID 14191082-Amino-4-methoxyphenolYield 93%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

20 g of 4-methoxy-2-nitrophenol was suspended in 350 ml of ethanol. Thereto was added 550 mg of 5% palladium-carbon. The mixture was subjected to hydrogenation at 20°-30° C. at atmospheric pressure. After the completion of the reaction, the catalyst was removed by filtration and then the solvent was removed by distillation under reduced pressure. The resulting crystal was recrystallized from isopropyl alcohol to obtain 15.3 g (yield: 93%) of 2-amino-4-methoxyphenol.

Workup

  1. customwas subjected to hydrogenation at 20°-30° C. at atmospheric pressure
  2. customAfter the completion of the reaction
  3. customthe catalyst was removed by filtration
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe resulting crystal was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-04603501057d47f39205eed2c545d4c5
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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