Water → 5-acetyl-2,3-dihydro-1H-indol-2-one

HRID 24326Notes

Reaction equation

HRID 24326 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[C:11](Cl)(=[O:13])[CH3:12].O>ClCCCl>[C:11]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][C:2](=[O:10])[CH2:3]2)(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 321710Oxindole

Product 1

HCID 102196435-acetyl-2,3-dihydro-1H-indol-2-oneYield 73%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

2-Oxindole (3 g) was suspended in 1,2-dichloroethane and 3.2 mL acetyl chloride were slowly added. The resulting suspension was heated to 50° C. for 5 hours, cooled, and poured into water. The resulting precipitate was collected by vacuum filtration, washed copiously with water and dried under vacuum to give 2.9 g (73% yield) of the title compound as a brown solid.

Workup

  1. temperaturecooled
  2. filtrationThe resulting precipitate was collected by vacuum filtration
  3. washwashed copiously with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-96f58ee0e61745fe9911b2aab6bbe5cd
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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