2,4-Dimethylphenol → 4-(2,4-Dimethylphenoxy)-6,7-dimethoxyquinoline

HRID 228510

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.[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=1[OH:24].[OH-].[Na+]>COCCOCCOC>[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=1[O:24][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

Participants

Conditions

Temperature: 180 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (200 mg) and 2,4-dimethylphenol (0.267 ml) were suspended in diethylene glycol dimethyl ether (0.1 ml), and the suspension was stirred at 180° C. for 1.5 hr. The reaction solution was cooled to room temperature, and an aqueous sodium hydroxide solution was then added to the reaction solution. The mixture was extracted with chloroform. The chloroform layer was then washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel using acetone-chloroform to give 4-(2,4-dimethylphenoxy)-6,7-dimethoxyquinoline (127 mg, yield 46%).

Workup

temperatureThe reaction solution was cooled to room temperature
extractionThe mixture was extracted with chloroform
washThe chloroform layer was then washed with 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 on silica gel

Sources & evidence

ORD record: ord-5ada81207d734a66b4327bce86f025a4
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Linked notes

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