Sodium Hydroxide → 3,3-Dimethyl-5-(trifluoromethyl)indolin-2-one

HRID 40482Notes

Reaction equation

HRID 40482 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([F:16])([F:15])[F:14])=[CH:10][CH:11]=2)[C:6]([CH3:18])([CH3:17])[C:5]1=[O:19])(=O)C.[OH-].[Na+]>C(O)C>[CH3:17][C:6]1([CH3:18])[C:7]2[C:12](=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:14])[F:15])[CH:8]=2)[NH:4][C:5]1=[O:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 580317261-Acetyl-3,3-dimethyl-5-trifluoromethyl-1,3-dihydroindol-2-one

Product 1

HCID 580317193,3-Dimethyl-5-(trifluoromethyl)indolin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

464 mg of 1-acetyl-3,3-dimethyl-5-trifluoromethyl-1,3-dihydroindol-2-one were dissolved in 4 ml of ethanol, and 1 ml of 1N sodium hydroxide solution was added. The reaction mixture was then stirred at room temperature for one hour. The reaction solution was extracted with 80 ml of methyl tert-butyl ether. The organic phase was washed with 30 ml of water and with 30 ml of saturated NaCl solution, dried over MgSO4 and concentrated under reduced pressure. This gave 354 mg of 3,3-dimethyl-5-trifluoromethyl-1,3-dihydroindol-2-one as a colorless solid.

Workup

  1. extractionThe reaction solution was extracted with 80 ml of methyl tert-butyl ether
  2. washThe organic phase was washed with 30 ml of water and with 30 ml of saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-856c41b67fe34ab2b73b0255509812d0
Source dataset
uspto-grants-2013_09
Patent number
US08530413B2

Reaction notes

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