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

HRID 1106724Notes

Reaction equation

HRID 1106724 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 11 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-9077e8e51b384e8a8500e94c7716b03b
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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