Isatin → 1H-Indole-2,3-dione, 1-benzoyl- (9CI)

HRID 1031959Notes

Reaction equation

HRID 1031959 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[H-].[Na+].[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[C:14]([N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7054IsatinHCID 7412Benzoyl chlorideHCID 24758Sodium hydride

Product 1

HCID 342001H-Indole-2,3-dione, 1-benzoyl- (9CI)Yield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14.7 g (0.10 mole) of isatin (dissolved in 100 ml of N,N-dimethylformamide) are added to 2.6 g (0.11 mole) of sodium hydride in 100 ml of N,N-dimethylformamide, while stirring. After the mixture has been stirred for one hour at room temperature, 14.1 g (0.10 mole) of benzoyl chloride are added dropwise at 0° C. Stirring is then continued for 10 minutes at 0° C. and the mixture is poured onto ice. The precipitate which separates out is filtered off under suction and dried to give 20 g (80%) of N-benzoylisatin as yellow crystals.

Workup

  1. stirringAfter the mixture has been stirred for one hour at room temperature
  2. stirringStirring
  3. additionthe mixture is poured onto ice
  4. filtrationThe precipitate which separates out is filtered off under suction
  5. customdried

Sources & evidence

ORD record
ord-deeece4a1be94020aaa15347646f9b86
Source dataset
uspto-grants-1990_09
Patent number
US04956387

Reaction notes

Loading…