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

HRID 53278Notes

Reaction equation

HRID 53278 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>C(OCC)(=O)C.CO.[Pt]=O>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([CH3:15])([CH3:1])[CH2:3][C:4]2=[O:14])=[CH:9][CH:8]=1

Participants

5

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 194.1%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,3-Dimethyl-6-nitro-indan-1-one (22.2 g, 54.1 mmol) and platinum oxide (0.44 g, 1.94 mmol) in 30 mL of ethyl acetate and 60 mL of methanol was hydrogenated on a Parr Shaker for 40 min. The mixture was filtered through a pad of celite. The filtrate was evaporated and the residue was triturated with hexane to give 18.4 g (97% yield) of the title product as yellow solids; 1H-NMR (CDCl3) δ1.38 (s, 6H), 2.56 (s, 2H), 6.98 (d, J=2.3 Hz, 1H), 7.02 (dd, J=2.3, 8.2 Hz, 1H), 7.30 (d, J=8.2 Hz, 1H); MS m/e 176 (MH+).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. customThe filtrate was evaporated
  3. customthe residue was triturated with hexane

Sources & evidence

ORD record
ord-5697b07f29b345b19481bc73d3d0af21
Source dataset
uspto-grants-1997_04
Patent number
US05618839

Reaction notes

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