Water → 4-(2-Cyclopentyloxy-quinolin-3-yloxy)-6,7-dimethoxy-quinoline

HRID 228841Notes

Reaction equation

HRID 228841 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:17]([OH:26])=[N:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2.C(=O)([O-])[O-].[K+].[K+].[CH:33]1(Br)[CH2:37][CH2:36][CH2:35][CH2:34]1.O>CN(C)C=O>[CH:33]1([O:26][C:17]2[C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 178486805HCID 178486805, compound

Product 1

HCID 230783834-(2-Cyclopentyloxy-quinolin-3-yloxy)-6,7-dimethoxy-quinolineYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6,7-Dimethoxy-4-(2-hydroxy-quinolin-3-yloxy)-quinoline (19 mg) was dissolved in N,N-dimethylformamide (4 ml) to prepare a solution. Potassium carbonate (180 mg) and cyclopentyl bromide (0.1 ml) 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 ethyl acetate. The organic layer was washed with water and was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography using acetone-chloroform to give the title compound (14 mg, yield 60%).

Workup

  1. customto prepare a solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under the reduced pressure
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1398dcb4d12146a4ad1099a0d5434194
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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