Water → Ethyl 2-(6,7-dimethoxyquinolin-4-yloxy)-5-methoxybenzoate

HRID 228624Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.C([O:18][C:19]1[C:20](=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)[C:21]([OH:23])=[O:22])C.O.Cl[C:32]1C=CC=C[C:33]=1Cl>CN(C)C1C=CN=CC=1>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:18][C:19]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:20]=1[C:21]([O:23][CH2:32][CH3:33])=[O:22]

Participants

Conditions

Temperature: 180 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (514 mg), ethyl 5-methoxysalicylic acid (1.35 g), and 4-dimethylaminopyridine (843 mg) were suspended in o-dichlorobenzene (8 ml), and the suspension was stirred at 180° C. for 4 hr. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give the title compound (152 mg, yield 170%).

Workup

temperatureThe reaction solution was cooled to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was then washed with water and saturated brine
dry with materialwas dried over anhydrous sodium sulfate
customThe solvent was removed
distillationby distillation under the reduced pressure
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-4cbeddd8ad1f4e89bf47dfeef17b0441
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Reaction notes

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