2,6-Dimethyl-3-pyridinol → 4-(2,6-Dimethyl-pyridin-3-yloxy)-6,7-dimethoxy-quinoline

HRID 228743

Reaction equation

[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.Cl[C:11]1[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[N:14]=[CH:13][CH:12]=1>CN(C1C=CN=CC=1)C.ClC1C=CC=CC=1Cl>[CH3:1][C:2]1[C:7]([O:8][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

2,6-Dimethylpyridin-3-ol (165 mg), 4-chloro-6,7-dimethoxyquinoline (100 mg), and 4-(N,N-dimethylamino)pyridine (164 mg) were dissolved in 1,2-dichlorobenzene (4.5 ml) to prepare a solution which was then stirred at 130° 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, the mixture was extracted with ethyl acetate, and the ethyl acetate layer was then washed with water and was 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 (116 mg, yield 83%).

Workup

customto prepare a solution which
temperatureThe reaction solution was cooled to room temperature
customthe solvent was then removed by distillation under the reduced pressure
additionWater was added to the residue
extractionthe mixture was extracted with ethyl acetate
washthe ethyl acetate layer was then washed with water
dry with materialwas dried over anhydrous sodium sulfate
customThe solvent was removed by distillation under the reduced pressure
customthe residue was purified by column chromatography

Sources & evidence

ORD record: ord-42c2f51ec9b6435aba4ee7014297329c
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07560558B2

Linked notes

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