Acetic Anhydride → 1-Acetylindolin-2-one

HRID 431038Notes

Reaction equation

HRID 431038 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-2dc8ae3de96a4b5fafda4a9e6938c27a
Source dataset
uspto-grants-2003_12
Patent number
US06656933B2

Reaction notes

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