Water → Methyl 3-[(6,7-dimethoxy-4-quinolyl)oxy]naphthalene-2-carboxylate

HRID 228603

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.[OH:16][C:17]1[C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1.O>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[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:16][C:17]1[C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][C:24]2[C:19]([CH:18]=1)=[CH:20][CH:21]=[CH:22][CH:23]=2

Participants

Conditions

Temperature: 150 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (100 mg), methyl 2-hydroxy-3-naphthoate (271 mg), and 4-dimethylaminopyridine (164 mg) were suspended in o-dichlorobenzene (6 ml), and the suspension was stirred at 150° C. for 2 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-chloroform to give the title compound (7 mg, yield 4%).

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-e71ebc302da742f38cfca225e11c4dbb
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Linked notes

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