Methyl iodide → 1-Acetyl-3,3-dimethyl-1,3-dihydro-indol-2-one

HRID 277723Notes

Reaction equation

HRID 277723 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C:5]1=O)(=[O:3])[CH3:2].I[CH3:15].[C:16](=[O:19])([O-])[O-].[K+].[K+]>CS(C)=O.O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH3:15])([CH3:5])[C:16]1=[O:19])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3237191-Acetylindolin-2-one

Product 1

HCID 8536071-Acetyl-3,3-dimethyl-1,3-dihydro-indol-2-oneYield 84%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of N-acetyl oxindole (2.0 g, 11.4 mmol), iodomethane (1.56 mL, 25.1 mmol) and potassium carbonate (3.1 g, 22.8 mmol) in DMSO (20 mL) was stirred at room temperature for 20 h. The reaction mixture was diluted with water. The resulting solids were filtered, washed with water and dried to give N-acetyl dimethyl oxindole as an orange solid (1.9 g, 84%).

Workup

  1. filtrationThe resulting solids were filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-bc6de7b2f10249f587b83f43d95a9523
Source dataset
uspto-grants-2002_03
Patent number
US06358945B1

Reaction notes

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