5-acetyl-2,3-dihydro-1H-indol-2-one → 5-Ethyl-1,3-dihydro-2H-indol-2-one

HRID 382486Notes

Reaction equation

HRID 382486 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)(=O)[CH3:2].[H][H]>[Pd].C(O)(=O)C>[CH2:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)[CH3:2]

Participants

5

Reactant 2

HCID 102196435-acetyl-2,3-dihydro-1H-indol-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 101541895-Ethyl-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

The 5-acetyloxindole (54 g, 308 mmol), acetic acid (400 ml) and palladium on carbon (10%, 5 g) are combined and treated with hydrogen for 14 hours at 55 psi. The catalyst is removed by filtering through a bed of Celite, the filtrate is concentrated under reduced pressure and the residue is treated with ether to give 5-ethyloxindole

Workup

  1. customThe catalyst is removed
  2. filtrationby filtering through a bed of Celite
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. additionthe residue is treated with ether

Sources & evidence

ORD record
ord-3610962f3bea498f9100a6bf509a0e4d
Source dataset
uspto-grants-2001_10
Patent number
US06310099B1

Reaction notes

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