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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 557403Generated: October 30, 2026

Acetic Acid → Methyl 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/557403

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantMethyl 3-aminocrotonateHCID 643918—
Reactant5-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 57438888—
ReactantSodium 1-cyanoprop-1-en-2-olateHCID 74083625—
SolventIsopropanolHCID 3776—
ProductMethyl 5-cyano-4-(5-fluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylateHCID 15979219—

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, 55.84 mg (0.49 mmol) of methyl 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. 128.3 mg (71.8% 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-45f146c5cbcc426fa4b5f387e35ae19d
Source noteuspto-grants-2011_11