Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 229018Generated: October 27, 2026

4-Quinolinecarboxylic acid, 3-hydroxy-2-methyl- → 6-Benzyloxy-7-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline

https://huagongshe.com/reaction/229018

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Quinolinecarboxylic acid, 3-hydroxy-2-methyl-HCID 67024—
Reactant6-(Benzyloxy)-4-chloro-7-methoxyquinolineHCID 23022781—
Catalyst4-(Dimethylamino)pyridineHCID 14284—
Solvent1,2-DichlorobenzeneHCID 7239—
Product6-Benzyloxy-7-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolineHCID 2307844163%

Reaction Conditions

Temperature150 °C

Reaction Steps

3-Hydroxy-2-methyl-4-quinoline carboxylic acid (549 mg), 6-benzyloxy-4-chloro-7-methoxyquinoline (810 mg), and 4-(N,N-dimethylamino)-pyridine (990 mg) were dissolved in 1,2-dichlorobenzene (40 ml) to prepare a solution. The mixture was stirred at 150° C. overnight. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. Water was added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using hexane-acetone to give the title compound (718 mg, yield 63%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07560558B2
Source datasetuspto-grants-2009_07
ORD IDord-8d3c988bb38246bea1b5dbe58048b442
Source noteuspto-grants-2009_07