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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1589651Generated: November 3, 2026

2-Chlorobenzaldehyde → 3-O-ethyl 5-O-methyl 2-(2-azidoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

https://huagongshe.com/reaction/1589651

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-ChlorobenzaldehydeHCID 6996—
Reactant2-AzidoethanolHCID 123118—
ReactantMethyl 3-aminocrotonateHCID 643918—
ReactantEthyl 4-(2-azidoethoxy)-3-oxobutanoateHCID 13663141—
SolventMethanolHCID 887—
Product3-O-ethyl 5-O-methyl 2-(2-azidoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylateHCID 309260629.9%

Reaction Steps

Ethyl 4-(2-azidoethoxy)acetoacetate (46.4 g), prepared from 2-azidoethanol similarly to the method described in Preparation 3, was reacted with methyl 3-aminocrotonate (24.8 g) and 2-chlorobenzaldehyde (30.3 g) in methanol (150 ml) at reflux for 18 hours. After cooling to room temperature, the resulting solid was collected, washed twice with methanol and dried to give the title compound (28 g). The product could be crystallised from methanol, acetone or ethyl acetate. It was used directly.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04572909
Source datasetuspto-grants-1986_02
ORD IDord-1898d73dc9674d45a98388837ce7fd60
Source noteuspto-grants-1986_02