Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 606106Generated: October 31, 2026

Ethyl orthopropionate → 4-chloro-2-ethyl-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinoline

https://huagongshe.com/reaction/606106

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl orthopropionateHCID 66995—
Reactant2-chloro-N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}quinoline-3,4-diamineHCID 86616890—
CatalystPyridinium chlorideHCID 10176127—
SolventTolueneHCID 1140—
Product4-chloro-2-ethyl-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinolineHCID 8661689167.9%

Reaction Conditions

Temperature110 °C

Reaction Steps

Under a nitrogen atmosphere, pyridine hydrochloride (0.020 g, 0.19 mmol), triethyl orthopropionate (2.5 g, 14 mmol), 2-chloro-N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}quinoline-3,4-diamine (3.5 g, 9.5 mmol), and toluene (50 mL) were combined and heated at 110° C. for 18 hours. Most of the volatiles were removed under reduced pressure to provide a suspension. The solid was isolated by filtration, washed with diethyl ether, and dried to provide 2.624 g of 4-chloro-2-ethyl-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinoline as a tan solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07915281B2
Source datasetuspto-grants-2011_03
ORD IDord-4d3566a0f6eb4e7e9b2f6ace7075bd34
Source noteuspto-grants-2011_03