3-Isopropylidene-4-methoxy-1,3-dihydro-indol-2-one → 3-Isopropyl-4-methoxy-1,3-dihydro-indol-2-one

HRID 1244840Notes

Reaction equation

HRID 1244840 reaction equation
[C:1](=[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:13][CH3:14])[NH:6][C:5]1=[O:15])([CH3:3])[CH3:2]>[Pd].C(O)C>[CH:1]([CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:13][CH3:14])[NH:6][C:5]1=[O:15])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 219232453-Isopropylidene-4-methoxy-1,3-dihydro-indol-2-one

Product 1

HCID 219232483-Isopropyl-4-methoxy-1,3-dihydro-indol-2-oneYield 80.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-isopropylidene-4-methoxy-1,3-dihydro-indol-2-one (700 mg, 3.4 mmol) and 5% palladium on carbon (88 mg) in ethanol (25 mL) is hydrogenated at 60 psi overnight. Filtration and removal of the solvent in vacuo provided 560 mg (79%) of 3-isopropyl-4-methoxy-1,3-dihydro-indol-2-one. MS (ESI+) 206.

Workup

  1. customis hydrogenated at 60 psi overnight
  2. filtrationFiltration and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-7ec73e1fa0a64052a7f8ae5efcf78d89
Source dataset
uspto-grants-2006_10
Patent number
US07122680B2

Reaction notes

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