Acetic Anhydride → 1-Acetylindolin-2-one

HRID 1744853Notes

Reaction equation

HRID 1744853 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-72b2ea7363b44d8e81fd08a47aed3a62
Source dataset
uspto-grants-2006_03
Patent number
US07019006B2

Reaction notes

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