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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 229015Generated: October 27, 2026

4-Quinolinecarboxylic acid, 3-hydroxy-2-methyl- → [6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yl]-(2-morpholin-4-yl-ethyl)-amine

https://huagongshe.com/reaction/229015

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Quinolinecarboxylic acid, 3-hydroxy-2-methyl-HCID 67024—
Reactant(4-Chloro-6-methoxy-quinolin-7-yl)-(2-morpholin-4-yl-ethyl)-amineHCID 23078325—
Catalyst4-(Dimethylamino)pyridineHCID 14284—
Solvent1,2-DichlorobenzeneHCID 7239—
Product[6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yl]-(2-morpholin-4-yl-ethyl)-amineHCID 2307837616.4%

Reaction Conditions

Temperature140 °C

Reaction Steps

(4-Chloro-6-methoxy-quinolin-7-yl)-(2-morpholin-4-yl-ethyl)-amine (53 mg), 3-hydroxy-2-methyl-quinolin-4-carboxylic acid (126 mg), and 4-dimethylaminopyridine (200 mg) were suspended in o-dichlorobenzene (8 ml). The suspension was stirred at 140° C. overnight. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using methanol-chloroform to give the title compound (12 mg, yield 16%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07560558B2
Source datasetuspto-grants-2009_07
ORD IDord-60f2c0707c31485a96b9c152ab20e237
Source noteuspto-grants-2009_07