4-Chlorobenzaldehyde → Z-6-chloro-3-(4-chloro-benzylidene)-1,3-dihydro-indol-2-one

HRID 1727966Notes

Reaction equation

HRID 1727966 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.[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.N1CCCCC1>CO>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:17]/[C:16]3[CH:19]=[CH:20][C:13]([Cl:12])=[CH:14][CH:15]=3)/[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 8082PiperidineHCID 7363446-Chloro-1,3-dihydroindol-2-one

Product 1

HCID 962924Z-6-chloro-3-(4-chloro-benzylidene)-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a manner similar to the method described in example 1a, 6-chlorooxindole (2 g, 11.4 mmol) was reacted with 4-chloro-benzaldehyde (1.91 g, 13.6 mmol) (1.53 g, 13.6 mmol) (Aldrich) and piperidine (1.34 mL, 13.6 mmol) in methanol to give a mixture of E- and Z-6-chloro-3-(4-chloro-benzylidene)-1,3-dihydro-indol-2-one as a yellow solid (Yield: 3.3 g, 100%).

Workup

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Sources & evidence

ORD record
ord-f3d248f9973c4263aac4ad8187e2aac3
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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