HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 228951Generated: October 27, 2026
4-Quinolinecarboxylic acid, 3-hydroxy-2-methyl- → 7-Benzyloxy-6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline
https://huagongshe.com/reaction/228951
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 4-Quinolinecarboxylic acid, 3-hydroxy-2-methyl- | HCID 67024 | — |
| Reactant | 7-(Benzyloxy)-4-chloro-6-methoxyquinoline | HCID 22646562 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | 1,2-Dichlorobenzene | HCID 7239 | — |
| Product | 7-Benzyloxy-6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline | HCID 23078517 | 85.1% |
Reaction Steps
3-Hydroxy-2-methyl-4-quinoline carboxylic acid (1.5 g), 7-benzyloxy-4-chloro-6-methoxyquinoline (2 g), and 4-(N,N-dimethylamino)-pyridine (2.4 g) were dissolved in 1,2-dichlorobenzene (70 ml) to prepare a solution which was then 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 and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography using hexane-acetone to give the title compound (2.4 g, yield 85%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07560558B2 |
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| Source dataset | uspto-grants-2009_07 |
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| ORD ID | ord-2ab71be221af4509892c785f01d651ca |
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| Source note | uspto-grants-2009_07 |
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