Sodium Hydroxide → 6-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

HRID 1942535Notes

Reaction equation

HRID 1942535 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:13])[CH:11]=2)[C:6]([CH3:15])([CH3:14])[C:5]1=[O:16])(=O)C.[OH-].[Na+]>CCO>[Br:13][C:10]1[CH:11]=[C:12]2[C:7]([C:6]([CH3:15])([CH3:14])[C:5](=[O:16])[NH:4]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 108267191-Acetyl-6-bromo-3,3-dimethylindolin-2-one

Product 1

HCID 106576496-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 1-acetyl-6-bromo-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (5.2 g) were added 1N aqueous NaOH solution (11 ml) and EtOH (44 ml), and the mixture was stirred at room temperature for one hour. After the reaction was complete, the solvent was concentrated, and thereto was added dropwise a 2N aqueous hydrochloric acid solution. The precipitated crystals were extracted with ethyl acetate, and this ethyl acetate solution was washed with water and an aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated. The obtained residue (4.1 g) was used in the subsequent reaction without further treatment.

Workup

  1. concentrationthe solvent was concentrated
  2. additionwas added dropwise a 2N aqueous hydrochloric acid solution
  3. extractionThe precipitated crystals were extracted with ethyl acetate
  4. washthis ethyl acetate solution was washed with water
  5. dry with materialan aqueous sodium chloride solution, dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe obtained residue (4.1 g) was used in the subsequent reaction without further treatment

Sources & evidence

ORD record
ord-25f6ec45238042daac82a1deb755f243
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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