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

HRID 361730Notes

Reaction equation

HRID 361730 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.[H][H]>C(O)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

5

Reactant 2

HCID 905626-Nitroindan-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 3128956-amino-2,3-dihydro-1H-inden-1-oneYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-Nitroindan-1-one (18.1 g, 102 mmol) was dissolved in ethanol (400 ml) and reduced using Pd (5%) on carbon (2.0 g) and 35 psi hydrogen pressure on a Parr apparatus. Filtration on celite followed by evaporation gave 6-aminoindan-1-one (13.7 g, 93 mmol). NMR (DMSO) 7.2 (d, J=7.7Hz, 1H), 6.9 (dd, Jab=7.7Hz, J ax=2.3 Hz, 1H), 6.75 (d, J=2.3Hz, 1H), 5.3 (brs, 2H), 2.9 (t, J=5.6 Hz, 2H), 2.55 (t, J=5.6 Hz, 2H).

Workup

  1. filtrationFiltration on celite
  2. customfollowed by evaporation

Sources & evidence

ORD record
ord-ce4e2cd074bf415985c4f80cbc1c49c2
Source dataset
uspto-grants-1999_02
Patent number
US05866612

Reaction notes

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