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

HRID 228953Notes

Reaction equation

HRID 228953 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[C:16]([CH3:25])=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2.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:13][C:12]1[CH:11]=[C:10]2[C:5]([C:6]([O:14][C:15]3[C:16]([CH3:25])=[N:17][C:18]4[C:23]([CH:24]=3)=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 1358548286-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-ol2×

Product 1

HCID 230782727-(2-Chloro-ethoxy)-6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolineYield 78.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-ol (compound 352) (200 mg) was dissolved in N,N-dimethylformamide (10 ml) to prepare a solution. 1-Bromo-2-chloroethane (432 mg) and potassium carbonate (416 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 sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (186 mg, yield 78%).

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 sodium 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-5ffdd3772eb74c4f8d9ce581175cf856
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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