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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 466539Generated: October 28, 2026

m-Toluidine → Ethyl 3-[(3-methylphenyl)amino]-1-pyrrolidinecarboxylate

https://huagongshe.com/reaction/466539

Reaction equation

Participants

RoleNameHCIDCharge
Reactantm-ToluidineHCID 7934—
ReactantThiopheneHCID 8030—
ReactantEthyl 3-oxopyrrolidine-1-carboxylateHCID 277754—
ReactantHCID 178418361HCID 178418361—
CatalystPalladiumHCID 23938—
SolventMethanolHCID 887—
ProductEthyl 3-[(3-methylphenyl)amino]-1-pyrrolidinecarboxylateHCID 15124798100%

Reaction Steps

A mixture of 7.9 parts of ethyl 3-oxo-1-pyrrolidinecarboxylate, 5.35 parts of 3-methylbenzenamine, 1 part of a solution of thiophene in methanol 4% and 200 parts of methanol was hydrogenated at normal pressure and at 50° C. with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated, yielding 12.4 parts (100%) of ethyl 3-[(3-methylphenyl)amino]-1-pyrrolidinecarboxylate as a residue (intermediate 19).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05157035
Source datasetuspto-grants-1992_10
ORD IDord-fd618134fae94c77b8df8f944252bc7d
Source noteuspto-grants-1992_10