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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 417238Generated: October 29, 2026

Piperidine → Z-6-chloro-3-(3-chloro-5-fluoro-benzylidene)-1,3-dihydro-indol-2-one

https://huagongshe.com/reaction/417238

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPiperidineHCID 8082—
Reactant6-Chloro-1,3-dihydroindol-2-oneHCID 736344—
Reactant3-Chloro-5-fluorobenzaldehydeHCID 2734839—
SolventMethanolHCID 887—
ProductZ-6-chloro-3-(3-chloro-5-fluoro-benzylidene)-1,3-dihydro-indol-2-oneHCID 8665393893.6%

Reaction Conditions

Temperature80 °C

Reaction Steps

To the mixture of 6-chloro-2-oxindole (4.4 g, 26 mmol) (Crescent) and 3-chloro-5-fluorobenzaldehyde (4.2 g, 26 mmol) (Aldrich) in methanol (200 mL) was added piperidine (2.3 g, 26 mmol) (Aldrich) dropwise. The mixture was then heated at 80° C. for 2 h. After cooled to 4° C., the mixture was filtered and resulting precipitate was collected, dried to give E/Z-6-chloro-3-(3-chloro-5-fluoro-benzylidene)-1,3-dihydro-indol-2-one as a yellow solid (Yield 7.5 g, 92%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08088815B2
Source datasetuspto-grants-2012_01
ORD IDord-351820dab05141fe95a65030707b7a6e
Source noteuspto-grants-2012_01