2'-Hydroxy-5'-methyl-3'-nitroacetophenone → 1-(3-Amino-2-hydroxy-5-methylphenyl)ethan-1-one

HRID 325725Notes

Reaction equation

HRID 325725 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[O:9])[C:5]([OH:11])=[C:4]([N+:12]([O-])=O)[CH:3]=1>C(O)C.[Pt]>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[O:9])[C:5]([OH:11])=[C:4]([NH2:12])[CH:3]=1

Participants

4

Reactant 1

HCID 7361622'-Hydroxy-5'-methyl-3'-nitroacetophenone

Product 1

HCID 27564491-(3-Amino-2-hydroxy-5-methylphenyl)ethan-1-oneYield 67.9%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-hydroxy-5-methyl-3-nitroacetophenone [4.0 g; Joshi et al., J. Amer. Chem. Soc., (1954), 76, 4993] in ethanol (150 ml) was hydrogenated at 25° C. and 3.5 kg/cm2 for 44 minutes using a catalyst of platinum on charcoal. The solution was filtered and the filtrate was evaporated at 30° C. under diminished pressure to give a dark red oil, which set to a semi-solid on standing overnight. This material was purified by chromatography on a column of silica gel using diethyl ether as eluant. The fastest running band (yellow) was collected to give 3-amino-2-hydroxy-5-methylacetophenone (2.3 g), m.p. 56°-58° C., in the form of a bright yellow solid.

Workup

  1. customwas hydrogenated at 25° C.
  2. filtrationThe solution was filtered
  3. customthe filtrate was evaporated at 30° C. under diminished pressure
  4. customto give a dark red oil, which
  5. waiton standing overnight
  6. customThis material was purified by chromatography on a column of silica gel
  7. customwas collected

Sources & evidence

ORD record
ord-bf8e981ac697496db81d977fc52f3b93
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Reaction notes

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