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

HRID 431532Notes

Reaction equation

HRID 431532 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 stiffed 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-c68775d28a204ab4b52e97ceecef4bd1
Source dataset
uspto-grants-2003_12
Patent number
US06660732B2

Reaction notes

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