Acetic Acid → 4-Methyl-6-acetamido-7-hydroxy-1-indanone

HRID 414678

Reaction equation

HRID 414678 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-])=O)[C:8]([OH:14])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:15].[C:16](O)(=[O:18])[CH3:17]>[C].[Pd]>[CH3:1][C:2]1[CH:10]=[C:9]([NH:11][C:16](=[O:18])[CH3:17])[C:8]([OH:14])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:15]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 136041424-Methyl-6-nitro-7-hydroxy-1-indanone

Product 1

HCID 136041464-Methyl-6-acetamido-7-hydroxy-1-indanone

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

Into a solution of 11.5 g of 4-methyl-6-nitro-7-hydroxy-1-indanone in 500 ml of acetic acid was added 1.5 g of 5% palladium carbon, then the mixture was subjected to a catalytic hydrogenation under an atmospheric pressure at a room temperature. The catalyst was removed by filtration and the solvent was removed by evaporation. The residue obtained was washed with ether and was recrystallized from methanol to obtain 6.34 g of 4-methyl-6-acetamido-7-hydroxy-1-indanone.

Workup

  1. customwas subjected to a catalytic hydrogenation under an atmospheric pressure at a room temperature
  2. customThe catalyst was removed by filtration
  3. customthe solvent was removed by evaporation
  4. customThe residue obtained
  5. washwas washed with ether
  6. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-acbcc05080a54311b75436cdf25ec350
Source dataset
uspto-grants-1988_12
Patent number
US04792628

Linked notes

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