Acetic Anhydride → 1-Acetylindolin-2-one

HRID 1795411Notes

Reaction equation

HRID 1795411 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(O)(=O)C.O>[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

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 321710Oxindole

Product 1

HCID 3237191-Acetylindolin-2-oneYield 79.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of oxindole (5.0 g, 37.5 mmol) in acetic anhydride (7.1 mL, 75.1 mmol) and acetic acid (25 mL) was refluxed for 20 h. After cooling to room temperature, the reaction mixture was diluted with water (200 mL). The resulting solids were filtered, washed with water and dried to give N-acetyl oxindole as a white solid (5.2 g, 79%).

Workup

  1. filtrationThe resulting solids were filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-2d25a8ecae304d7fa5cb2c223a89712e
Source dataset
uspto-grants-2006_04
Patent number
US07026476B2

Reaction notes

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