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

HRID 483601Notes

Reaction equation

HRID 483601 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.[C].[Pd]>[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 97.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 200 ml of ethanol was dissolved 4.0 g (20.5 mmol) of 2-hydroxy-5-methyl-3-nitroacetophenone, and the mixture was stirred at room temperature for about 2 hours in the presence of 1.0 g of 5% palladium carbon while bubbling hydrogen gas thereinto. The inorganic substance was filtered off, and the filtrate was concentrated to obtain 3.30 g (yield: 97%) of 3-amino-2-hydroxy-5-methylacetophenone as brown needle crystals.

Workup

  1. customwhile bubbling hydrogen gas
  2. filtrationThe inorganic substance was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b0435875dd70481597ffa445d32be724
Source dataset
uspto-grants-1993_07
Patent number
US05225559

Reaction notes

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