Methyl iodide → 5-Chloro-3-methyl-3-phenyl-1,3-dihydro-2H-indol-2-one

HRID 65448Notes

Reaction equation

HRID 65448 reaction equation
[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:16])[CH:14]=3)[NH:9][C:8]2=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O.O>[CH3:18][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:16])[CH:14]=2)[NH:9][C:8]1=[O:17]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 190764863-Phenyl-5-chlorooxindole

Product 1

HCID 202330995-Chloro-3-methyl-3-phenyl-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

10 g of 3-phenyl-5-chlorooxindole were dissolved in 100 ml of acetone and 20 ml of water, 2.9 g of potassium carbonate and 2.9 ml of methyl iodide were added and the mixture was warmed at 50° C. for 3 hours and concentrated; water was added to the residue, which was extracted with ethyl acetate, and the extract was dried over magnesium sulfate, and the solvent was removed. The residue was recrystallized from ethanol. Melting point 180°-181° C.

Workup

  1. concentrationconcentrated
  2. additionwater was added to the residue, which
  3. extractionwas extracted with ethyl acetate
  4. dry with materialthe extract was dried over magnesium sulfate
  5. customthe solvent was removed
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-360c2f98109549b791910c86c16f8403
Source dataset
uspto-grants-1986_09
Patent number
US04614739

Reaction notes

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