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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 557402Generated: October 30, 2026

Acetic Acid → Ethyl 5-cyano-4-(5-fluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylate

https://huagongshe.com/reaction/557402

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
Reactant2-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 643756—
Reactant5-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 57438888—
ReactantSodium 1-cyanoprop-1-en-2-olateHCID 74083625—
SolventIsopropanolHCID 3776—
ProductEthyl 5-cyano-4-(5-fluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylateHCID 15979092—

Reaction Steps

A solution of 100 mg (0.49 mmol) of 5-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde in 5 ml of 2-propanol is mixed with 50.96 mg (0.49 mmol) of sodium 1-cyanoprop-1-en-2-olate, 62.65 mg (0.49 mmol) of ethyl 3-aminocrotonate and 0.04 ml (0.73 mmol) of acetic acid and stirred under reflux for 3 h. After cooling, the mixture is concentrated. The residue is taken up in dichloromethane and washed with water. The organic phase is dried over sodium sulfate and concentrated. The resulting residue is crystallized from diethyl ether. The beige-colored crystals are filtered off with suction and dried at 40° C. in a vacuum drying oven. 120.7 mg (65.1% of theory) of the title compound are obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08058447B2
Source datasetuspto-grants-2011_11
ORD IDord-4e30f5ffb4ce4981b48e72e20c3da914
Source noteuspto-grants-2011_11