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

HRID 1696493Notes

Reaction equation

HRID 1696493 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>CO.[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

4

Reactant 1

HCID 905626-Nitroindan-1-one

Product 1

HCID 3128956-amino-2,3-dihydro-1H-inden-1-oneYield 87.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the 6-nitroindan-1-one (10 g, 56 mmol) and 10% Pd/C (2.0 g) in MeOH (200 mL) was stirred under 30 psi of H2 at RT for 3 h. After filtration, the filtrate was concentrated to afford 6-aminoindan-1-one (7.2 g, 87% yield). 1H NMR (300 MHz, DMSO-d6): δ 7.17 (d, J1=8.1 Hz, 1H), 6.87 (d, J=8.1 Hz, 1H), 6.71 (s, 1H), 5.24 (s, 2H), 2.85 (t, J=5.4 Hz, 2H), 2.49 (t, J=5.7 Hz, 2H).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-42f618827b3348a88249eb3448daf254
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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