Water → 6-(2-Chloroethoxy)-7-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline

HRID 229020Notes

Reaction equation

HRID 229020 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][C:14]3[C:15]([CH3:24])=[N:16][C:17]4[C:22]([CH:23]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[OH:25].Br[CH2:27][CH2:28][Cl:29].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:29][CH2:28][CH2:27][O:25][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[N:10]=[CH:9][CH:8]=[C:7]2[O:13][C:14]1[C:15]([CH3:24])=[N:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2

Participants

6

Reactant 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 230782657-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-6-ol

Product 1

HCID 230784836-(2-Chloroethoxy)-7-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolineYield 80.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-6-ol (25 mg) was dissolved in N,N-dimethylformamide (1 ml) to prepare a solution. 1-Bromo-2-chloroethane (54 mg) and potassium carbonate (52 mg) were added to the solution, and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin layer chromatography using chloroform-methanol to give 6-(2-chloroethoxy)-7-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline (24 mg, yield 79%).

Workup

  1. customto prepare a solution
  2. extractionthe mixture was extracted with chloroform
  3. washThe chloroform layer was washed with water
  4. dry with materialwas then dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customThe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-8380dd78c1b24536bc4be3a4b5a281b2
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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