Imidazole → 6-(2-Imidazol-1-yl-ethoxy)-7-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline

HRID 229021Notes

Reaction equation

HRID 229021 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][CH:9]=[C:8]2[O:17][C:18]1[C:19]([CH3:28])=[N:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2.C(=O)([O-])[O-].[K+].[K+].[NH:35]1[CH:39]=[CH:38][N:37]=[CH:36]1.[I-].[Na+]>CN(C)C=O>[N:35]1([CH2:2][CH2:3][O:4][C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][C:14]=2[O:15][CH3:16])[N:11]=[CH:10][CH:9]=[C:8]3[O:17][C:18]2[C:19]([CH3:28])=[N:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:39]=[CH:38][N:37]=[CH:36]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 230784836-(2-Chloroethoxy)-7-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline

Product 1

HCID 230782606-(2-Imidazol-1-yl-ethoxy)-7-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolineYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

N,N-Dimethylformamide (3 ml) was added to 6-(2-chloro-ethoxy)-7-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinoline (24 mg), potassium carbonate (25 mg), imidazole (12 mg), and sodium iodide (1.8 mg), and the mixture was stirred at 75° C. overnight. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (9.2 mg, yield 36%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was removed by distillation under the reduced pressure
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialwas then 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-7d188a0d59084fa4beb92ac09c40c76c
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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