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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 4669Generated: October 25, 2026

Methyl acetoacetate → dimethyl 4-[2-[(E)-4-chloro-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

https://huagongshe.com/reaction/4669

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl acetoacetateHCID 7757—
ReactantMethyl 3-aminocrotonateHCID 643918—
Reactant2-[(E)-4-chloro-2-butenyloxy]-5-nitrobenzaldehydeHCID 14050496—
SolventIsopropanolHCID 3776—
Productdimethyl 4-[2-[(E)-4-chloro-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylateHCID 1405049748.8%

Reaction Steps

5.2 g of 2-[(E)-4-chloro-2-butenyloxy]-5-nitrobenzaldehyde, 2.4 g of methyl acetoacetate and 2.3 g of methyl 3-aminocrotonate was dissolved in 30 ml of iso-propanol, and the solution obtained was refluxed for 3.5 hours under heating. After cooling, the precipitated crystals were collected by filtration to give 4.4 g of dimethyl 4-[2-[(E)-4-chloro-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. (mp. 206°-207° C.). The product obtained was used directly for the next process without purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04727082
Source datasetuspto-grants-1988_02
ORD IDord-062c826e74c641139e59148b875c82f5
Source noteuspto-grants-1988_02