Isatin → N-Benzoylisatin

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

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.