2-Methyl-3-nitrophenol → 2-Amino-o-cresol

HRID 618218Notes

Reaction equation

HRID 618218 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11]>C(O)C.[Pd]>[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11]

Participants

4

Reactant 1

HCID 795792-Methyl-3-nitrophenol

Product 1

HCID 1044482-Amino-o-cresolYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-methyl-3-nitrophenol (25 g, 0.163 mol) was dissolved in 170 ml of absolute ethanol in a 1 l Parr hydrogenation flask. The flask was purged with nitrogen. 10% palladium on charcoal (1.73 g, 1.6 mmol) was added and the mixture was hydrogenated (40 psi H2) for 1.5 hr in a Parr apparatus. The flask was evacuated and purged with nitrogen. The catalyst was removed by filtration through a Whatman GF/F filter. After removal of the ethanol at reduced pressure, 20.1 g (100% yield) of 2-methyl-3-aminophenol was obtained as a lightly brown solid.

Workup

  1. customThe flask was purged with nitrogen
  2. customfor 1.5 hr
  3. customThe flask was evacuated
  4. custompurged with nitrogen
  5. customThe catalyst was removed by filtration through a Whatman GF/F
  6. filtrationfilter
  7. customAfter removal of the ethanol at reduced pressure

Sources & evidence

ORD record
ord-9a81a63f0b62479fa58165c2c56a8920
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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