3,3-Dimethylindan-1-one oxime → 3,3-dimethyl-2,3-dihydro-1H-inden-1-amine

HRID 222186Notes

Reaction equation

HRID 222186 reaction equation
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[N:11]O)[CH2:3]1>CO.[Pd]>[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([NH2:11])[CH2:3]1

Participants

4

Reactant 1

HCID 866142543,3-Dimethylindan-1-one oxime

Product 1

HCID 230089363,3-dimethyl-2,3-dihydro-1H-inden-1-amineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3,3-Dimethylindan-1-one oxime (1.22 g, 6.96 mmol) was dissolved in MeOH (20.0 mL) and palladium (10 weight percent on carbon, 50% water wet, 148 mg) was added. The reaction was placed under an atmosphere of hydrogen and was stirred overnight. The mixture was then filtered through Celite, washed through with MeOH and the filtrates concentrated in vacuo to afford the product as a grey oil (1.12 g, 100%). LC/MS: Rt=1.04 min, ES+ 162 (AA standard).

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. washwashed through with MeOH
  3. concentrationthe filtrates concentrated in vacuo

Sources & evidence

ORD record
ord-6c265b8c4dfc4ca2bf2533e06d1d7952
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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