4-Chloro-6,7-dimethoxyquinoline → {4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}(3-methylphenyl)methanone

HRID 228602Notes

Reaction equation

HRID 228602 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.Cl[C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][CH:19]=1.C(=O)([O-])O.[Na+]>C1(C)C(C)=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:29][O:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[O:30][CH3:31])[N:21]=[CH:20][CH:19]=[C:18]2[O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH:11]=2)=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 516892Sodium BicarbonateHCID 22132621(4-Hydroxyphenyl)(3-methylphenyl)methanone

Product 1

HCID 22132753{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}(3-methylphenyl)methanoneYield 45.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 7237O-XyleneSolvent

Procedure

(4-Hydroxyphenyl)(3-methylphenyl)methanone (307 mg) was dissolved in xylene to prepare a solution. 4-Dimethylaminopyridine (194 mg) and 4-chloro-6,7-dimethoxyquinoline (342 mg) were added to the solution, and the mixture was heated under reflux for 23 hr. A saturated aqueous sodium hydrogencarbonate solution was added thereto, and the mixture was extracted with chloroform. The organic layer was dried over sodium sulfate and was then concentrated. The residue was subjected to separation and purification by column chromatography on silica gel using hexane-ethyl acetate, chloroform, and hexane-acetone as solvents to give the title compound (262 mg, yield 45%).

Workup

  1. customto prepare a solution
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 23 hr
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationwas then concentrated
  7. customThe residue was subjected to separation and purification by column chromatography on silica gel

Sources & evidence

ORD record
ord-0d73da514de344d991d51c555b9744c7
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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