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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 557409Generated: October 29, 2026

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

https://huagongshe.com/reaction/557409

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
Reactant5,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 57438889—
ReactantCyclobutyl 3-aminocrotonateHCID 57475512—
ReactantSodium 1-cyanoprop-1-en-2-olateHCID 74083625—
SolventIsopropanolHCID 3776—
ProductCyclobutyl 5-cyano-4-(5,6-difluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylateHCID 15979223—

Reaction Steps

A solution of 100 mg (0.45 mmol) of 5,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde in 5 ml of 2-propanol is mixed with 46.9 mg (0.45 mmol) of sodium 1-cyanoprop-1-en-2-olate, 69.23 mg (0.45 mmol) of cyclobutyl 3-aminocrotonate and 0.04 ml (0.67 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 yellow crystals are filtered off with suction and dried in a vacuum drying oven at 40° C. 104.4 mg (54.9% 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-f2d1f9b5980e4bd8bec9987d316855bd
Source noteuspto-grants-2011_11