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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2427407Generated: November 1, 2026

Triazabicyclodecene → 4-methyl-3-p-tolyl-1H-pyrrole-2-carboxylic acid ethyl ester

https://huagongshe.com/reaction/2427407

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriazabicyclodeceneHCID 79873—
ReactantEthyl isocyanoacetateHCID 533707—
Reactant4-Methyl-beta-ethyl-beta-nitrostyreneHCID 66883569—
SolventIsopropanolHCID 3776—
SolventTetrahydrofuranHCID 8028—
Product4-methyl-3-p-tolyl-1H-pyrrole-2-carboxylic acid ethyl esterHCID 1561324385%

Reaction Steps

1,5,7-Triazabicyclo[4.4.0]dec-5-ene on polystyrene (5.36 g, 2.6 mmol/g, 13.9 mmol) was added to a reaction mixture of 4-methyl-β-ethyl-β-nitrostyrene (1.23 g, 6.94 mmol) and isocyanoacetic acid ethyl ester (788 mg, 6.90 mmol) in isopropanol (5 mL) and THF (5 mL) and the reaction mixture was stirred overnight at RT under nitrogen as protective gas. The reaction mixture was filtered out and the residue washed with isopropanol and THF. The desired product 4-methyl-3-p-tolyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.42 g, 85% of theoretical) was obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07968591B2
Source datasetuspto-grants-2011_06
ORD IDord-eea1f965d4cf40fe8f05ff38e951ec8b
Source noteuspto-grants-2011_06