Acetic Anhydride → 1-Acetylindolin-2-one

HRID 555658Notes

Reaction equation

HRID 555658 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](OC(=O)C)(=[O:13])[CH3:12]>>[C:11]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10])(=[O:13])[CH3:12]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 321710Oxindole

Product 1

HCID 3237191-Acetylindolin-2-one

Procedure

Oxindole (1 equivalent) was dissolved in acetic anhydride and the resulting mixture was heated under reflux for 3 days. After cooling, the reaction mixture was poured into ice water. The resulting precipitate was collected by filtration, washed with water and dried, whereby 1-acetyloxindole was obtained. From the thus obtained 1-acetyloxindole and diformylfuran, a target compound was obtained in the same manner as in Example 1.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 3 days
  3. temperatureAfter cooling
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-438e912d49544eb685e950a157d3471d
Source dataset
uspto-grants-2011_11
Patent number
US08053461B2

Reaction notes

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