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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 322197Generated: October 27, 2026

Methyl 3-aminocrotonate → 2-(4-Azidobutyl)-3-(2-cyanoethoxy) carbonyl-1,4-dihydro-5-methoxycarbonyl-6-methyl-4-(4-nitrophenyl)pyridine

https://huagongshe.com/reaction/322197

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl 3-aminocrotonateHCID 643918—
Reactant7-Azido-2-[(4-nitrophenyl)methylene]-3-oxoheptanoic acid 2-cyanoethyl esterHCID 53869981—
SolventEthanolHCID 702—
Product2-(4-Azidobutyl)-3-(2-cyanoethoxy) carbonyl-1,4-dihydro-5-methoxycarbonyl-6-methyl-4-(4-nitrophenyl)pyridineHCID 86586635—

Reaction Steps

A solution of 7-azido-2-[(4-nitrophenyl)methylene]-3-oxoheptanoicacid2-cyanoethyl ester (2.87 g, 7.73 mmol) and methyl 3-aminocrotonate (0.900 g, 7.73 mmol) in 50 ml of EtOH was refluxed for 48 hrs. After the EtOH was removed in vacuo, the residue was dissolved in 150 ml of CHCl3, washed with water (2×100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, the product was purified by chromatography (SiO2, CHCl3:MeOH=95:5). 2-(4-Azidobutyl)-3-(2-cyanoethoxy)carbonyl-1,4-dihydro-5-methoxycarbonyl-6-methyl-4-(4-nitrophenyl)pyridine was obtain as a yellow oil (2.43 g, 67% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06211198B1
Source datasetuspto-grants-2001_04
ORD IDord-fb08d28a959f4af8be806c43b0033d3e
Source noteuspto-grants-2001_04