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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1728190Generated: October 27, 2026

Pyrrolidine → 6-Chloro-3-(5-chloro-pyridine-3-ylmethylene)-1,3-dihydro-indol-2-one

https://huagongshe.com/reaction/1728190

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyrrolidineHCID 31268—
Reactant6-Chloro-1,3-dihydroindol-2-oneHCID 736344—
Reactant5-Chloro-pyridine-3-carbaldehydeHCID 14444196—
ReactantZ-6-chloro-3-(5-chloro-pyridine-3-ylmethylene)-1,3-dihydro-indol-2-oneHCID 68956604—
SolventMethanolHCID 887—
Product6-Chloro-3-(5-chloro-pyridine-3-ylmethylene)-1,3-dihydro-indol-2-oneHCID 68956605—

Reaction Conditions

Temperature70 °C

Reaction Steps

To the mixture of 6-chlorooxindole (0.93 g, 5.6 mmol) and 5-chloro-pyridine-3-carbaldehyde (0.8 g, 5.6 mmol) in methanol (10 mL) was added pyrrolidine (0.6 g, 5.6 mmol) dropwise. The mixture was then heated at 70° C. for 3 h and cooled to room temperature. The precipitate was collected, dried to give a mixture of E/Z-6-chloro-3-(5-chloro-pyridine-3-ylmethylene)-1,3-dihydro-indol-2-one as a bright yellow solid (Yield 1.0 g, 63%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07495007B2
Source datasetuspto-grants-2009_02
ORD IDord-3c636d0d8f7249faae9abea1b1efb620
Source noteuspto-grants-2009_02