Benzaldehyde → 3-Benzylidene-6-chloroindolin-2-one

HRID 1727974Notes

Reaction equation

HRID 1727974 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1CCCC1>CO>[CH:12](=[C:6]1/[C:7](=[O:11])[NH:8][C:9]2[C:5]/1=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 31268PyrrolidineHCID 7363446-Chloro-1,3-dihydroindol-2-one

Product 1

HCID 9629043-Benzylidene-6-chloroindolin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in example 1a, 6-chlorooxindole (1.0 g, 5.7 mmol) was reacted with benzaldehyde (0.6 g, 5.7 mmol) (Aldrich) and pyrrolidine (0.4 g, 5.7 mmol) in methanol to give a mixture of E- and Z-3-benzylidene-6-chloro-1,3-dihydro-indol-2-one as a yellow solid (Yield 1.5 g, 100%).

Workup

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Sources & evidence

ORD record
ord-6ed43f39301540479e32a3e2acfb7e23
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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