Dichloromethane → 6-amino-2,3-dihydro-1H-inden-1-one

HRID 1661372Notes

Reaction equation

HRID 1661372 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][C:10]2=[O:13])=[CH:6][CH:5]=1)([O-])=O.ClCCl.C(OCC)(=O)C>CO.[C].[Pd]>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][C:10]2=[O:13])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 905626-Nitroindan-1-one

Product 1

HCID 3128956-amino-2,3-dihydro-1H-inden-1-oneYield 81%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

6-Nitro-1-indanone (10.0 g, 56.4 mmol) was dissolved in methanol (200 mL), a 10% palladium-carbon powder (500 mg) was added, and the mixture was stirred at room temperature for 14 hr under a hydrogen atmosphere. To the reaction solution were added dichloromethane and ethyl acetate to dissolve the precipitated crystals, and the catalyst was filtered off. The filtrate was concentrated under reduced pressure, and the residue was washed with methanol to give the title compound (6.71 g, yield 81%).

Workup

  1. dissolutionto dissolve the precipitated crystals
  2. filtrationthe catalyst was filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washthe residue was washed with methanol

Sources & evidence

ORD record
ord-806b8c2f96664f3badca5f284f2d11f9
Source dataset
uspto-grants-2011_10
Patent number
US08030337B2

Reaction notes

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