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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1582958Generated: October 27, 2026

4-Cyanobutanoic acid → 4-(3-chlorophenyl)-3-(2-cyanoethyl)-1-ethyl-7-methyl-1,8-naphthyridin-2(1H)-one

https://huagongshe.com/reaction/1582958

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Cyanobutanoic acidHCID 38239—
ReactantPivaloyl chlorideHCID 62493—
ReactantSodium MethoxideHCID 10942334—
Reactant3-(3-Chlorobenzoyl)-2-ethylamino-6-methylpyridineHCID 11054902—
SolventEthanolHCID 702—
SolventMethanolHCID 887—
SolventTetrahydrofuranHCID 8028—
Product4-(3-chlorophenyl)-3-(2-cyanoethyl)-1-ethyl-7-methyl-1,8-naphthyridin-2(1H)-oneHCID 12991188—

Reaction Steps

After the treatment of 4-cyanobutanoic acid with sodium methoxide in methanol, the treated compound was reacted with pivaloyl chloride in THF. Thus obtained compound was reacted with 3-(3-chlorobenzoyl)-2-ethylamino-6-methylpyridine under heating. Then, the compound obtained by usual work-up was reacted in ethanol in the presence of sodium methoxide under heating. Thereafter, the reaction mixture was worked up and purified in a usual manner to obtain 4-(3-chlorophenyl)-3-(2-cyanoethyl)-1-ethyl-7-methyl-1,8-naphthyridin-2(1H)-one as a pale yellow solid. MS: 352.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06740662B1
Source datasetuspto-grants-2004_05
ORD IDord-d654fb4d8c834d78a26cd3595d5d459f
Source noteuspto-grants-2004_05