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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1728222Generated: November 2, 2026

Pyrrolidine → 4-Chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-benzoic acid methyl ester

https://huagongshe.com/reaction/1728222

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyrrolidineHCID 31268—
Reactant6-Chloro-1,3-dihydroindol-2-oneHCID 736344—
Reactantmethyl 4-chloro-2-formylbenzoateHCID 57566138—
ReactantHCID 86760834HCID 86760834—
SolventMethanolHCID 887—
Product4-Chloro-2-(6-chloro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-benzoic acid methyl esterHCID 57566241—

Reaction Conditions

Temperature70 °C

Reaction Steps

To the mixture of 6-chlorooxindole (1.2 g, 7 mmol) and 4-chloro-2-formyl-benzoic acid methyl ester (1.4 g, 7 mmol) in methanol (10 mL) was added pyrrolidine (490 mg, 7 mmol) dropwise. The mixture was then heated at 70° C. for 3 h. After cooled to 4° C., the mixture was filtered and the precipitate was collected, dried to give a mixture of E/Z-6-chloro-3-(5-chloro-2-hydroxy-benzylidene)-1,3-dihydro-indol-2-one as a bright yellow solid (500 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07495007B2
Source datasetuspto-grants-2009_02
ORD IDord-26e00217062d4bec9889aa95da59b997
Source noteuspto-grants-2009_02