4-Chloro-6,7-dimethoxyquinoline → HCID 57756335, compound

HRID 228839Notes

Reaction equation

HRID 228839 reaction equation
[OH:1][C:2]1[C:3]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl[C:21]1[C:30]2[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=2)[N:24]=[CH:23][CH:22]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:32][O:31][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][C:27]=1[O:33][CH3:34])[N:24]=[CH:23][CH:22]=[C:21]2[O:1][C:2]1[C:3]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 23078404HCID 23078404, compound

Product 1

HCID 57756335HCID 57756335, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
150 °C

Procedure

(3-Hydroxy-quinolin-2-yl)-phenyl-methanone (27 mg), 4-chloro-6,7-dimethoxyquinoline (120 mg), and 4-dimethylaminopyridine (147 mg) were suspended in o-dichlorobenzene (5 ml), and the suspension was stirred at 150° C. for 2 hr. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was 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 thin layer chromatography using acetone-chloroform to give the title compound (20 mg, yield 42%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was removed by distillation under the reduced pressure
  3. additionWater was then added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customthe solvent was removed by distillation under the reduced pressure
  8. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-baa864fd6cb742769ba68e546211d733
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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