4-Quinolinecarboxylic acid, 3-hydroxy-2-methyl- → 7-Benzyloxy-6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline

HRID 228951Notes

Reaction equation

HRID 228951 reaction equation
[OH:1][C:2]1[C:3]([CH3:15])=[N:4][C:5]2[C:10]([C:11]=1C(O)=O)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:16]([O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28](Cl)=[CH:29][CH:30]=[N:31]2)=[CH:26][C:25]=1[O:35][CH3:36])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C1C=CN=CC=1)C.ClC1C=CC=CC=1Cl>[CH2:16]([O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28]([O:1][C:2]3[C:3]([CH3:15])=[N:4][C:5]4[C:10]([CH:11]=3)=[CH:9][CH:8]=[CH:7][CH:6]=4)=[CH:29][CH:30]=[N:31]2)=[CH:26][C:25]=1[O:35][CH3:36])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 670244-Quinolinecarboxylic acid, 3-hydroxy-2-methyl-HCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinoline

Product 1

HCID 230785177-Benzyloxy-6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolineYield 85.1%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
150 °C

Procedure

3-Hydroxy-2-methyl-4-quinoline carboxylic acid (1.5 g), 7-benzyloxy-4-chloro-6-methoxyquinoline (2 g), and 4-(N,N-dimethylamino)-pyridine (2.4 g) were dissolved in 1,2-dichlorobenzene (70 ml) to prepare a solution which was then stirred at 150° 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, and the mixture was extracted with chloroform and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography using hexane-acetone to give the title compound (2.4 g, yield 85%).

Workup

  1. customto prepare a solution which
  2. temperatureThe reaction solution was cooled to room temperature
  3. customthe solvent was then removed by distillation under the reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with chloroform
  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 column chromatography

Sources & evidence

ORD record
ord-2ab71be221af4509892c785f01d651ca
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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