1-Acetyl-3,3-dimethyl-1,3-dihydro-indol-2-one → 3,3-Dimethyl-1,3-dihydro-indol-2-one

HRID 431533Notes

Reaction equation

HRID 431533 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH3:14])([CH3:13])[C:5]1=[O:15])(=O)C>S(=O)(=O)(O)O.C1COCC1.CCOCC>[CH3:13][C:6]1([CH3:14])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][C:5]1=[O:15]

Participants

5

Reactant 1

HCID 8536071-Acetyl-3,3-dimethyl-1,3-dihydro-indol-2-one

Product 1

HCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-oneYield 57%

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-acetyl dimethyl oxindole (500 mg, 2.5 mmol) in 3 N sulfuric acid solution (7 mL) and THF (7 mL) was refluxed for 4 h. After cooling to room temperature, the reaction mixture was diluted with ether. The ethereal layer was washed with water and brine, dried (magnesium sulfate), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluent: 30% EtOAc in hexanes) to give dimethyl oxindole as a red solid (228 mg, 57%).

Workup

  1. washThe ethereal layer was washed with water and brine
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (eluent: 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1d9628be8a14406a807b775902492ad6
Source dataset
uspto-grants-2003_12
Patent number
US06660732B2

Reaction notes

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