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

HRID 1380153Notes

Reaction equation

HRID 1380153 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[H][H]>O1CCCC1.CO.[Pd]>[NH2:8][C:7]1[C:2]([CH3:1])=[C:3]([OH:11])[CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 795792-Methyl-3-nitrophenolHCID 178418361HCID 178418361, compound

Product 1

HCID 1044482-Amino-o-cresol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Methyl-3-nitrophenol (70 g) in 100 ml of tetrahydrofuran and 400 ml of methanol at room temperature was hydrogenated under 5 psi of hydrogen gas using 3.5 g of 5% palladium on carbon as catalyst. After removal of catalyst by filtration, the filtrate was concentrated to give 56 g of analytically pure 3-amino-2-methylphenol. This aminophenol was then converted to the title compound (7.9 g) using the general method of Example 2, except that the hydrochloride salt was formed by adding hydrogen chloride/dioxane to a methanol solution of the free base. The nmr spectrum and elemental analysis were in agreement with those of title compound prepared by Example 3 (Method A).

Workup

  1. customat room temperature
  2. customAfter removal of catalyst
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f18a8c348f12494e996a0c21812d76d1
Source dataset
uspto-grants-1986_04
Patent number
US04579951

Reaction notes

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