3,3-dimethyl-6-nitro-2,3-dihydro-1H-inden-1-one → 6-Amino-3,3-dimethylindan-1-one

HRID 1609697Notes

Reaction equation

HRID 1609697 reaction equation
[CH3:1][C:2]1([CH3:15])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[C:4](=[O:14])[CH2:3]1>CO.[Pd]>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[C:2]([CH3:1])([CH3:15])[CH2:3][C:4]2=[O:14]

Participants

4

Reactant 1

HCID 124417863,3-dimethyl-6-nitro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 124417896-Amino-3,3-dimethylindan-1-oneYield 1,029.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1,1-dimethyl-5-nitro-indan-3-one (6.5 g, 3.17 mmoles, prepared according to part D of Example 1) in methanol (150 ml) containing 5% palladium on carbon (0.75 g) was stirred under hydrogen gas at 15 psi for four hours. The catalyst was filtered and the methanol was recovered under vacuum to obtain a green solid (5.72 g). The reaction product was used in the next step without further purification. 1H NMR (CDCl3) δ 7.26 (d, J=8.20 Hz, 1H), 6.95 (m, 2H), 3.82 (broad s, 2H), 2.55 (s, 2H), 1.36 (s, 6H); 13C NMR (CDCl3) δ 206.25, 154.53, 146.05, 136.27, 124.04, 123.03, 107.14, 53.41, 37.74, 30.04.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe methanol was recovered under vacuum

Sources & evidence

ORD record
ord-da2548f3f2f2474e9b2484ac179d6ba1
Source dataset
uspto-grants-1995_03
Patent number
US05401848

Reaction notes

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