Water → HCID 23078381, compound

HRID 229024Notes

Reaction equation

HRID 229024 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:16][C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2.[H-].[Na+].O>CC(N(C)C)=O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[NH:16][C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][CH:21]=2

Participants

6

Reactant 4

HCID 962WaterHCID 113753-AminoquinolineHCID 24758Sodium hydrideHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 23078381HCID 23078381, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

4-Chloro-6,7-dimethoxyquinoline (88 mg) and 3-aminoquinoline (72 mg) were dissolved in dimethylacetamide (1 ml) to prepare a solution. 60% sodium hydride (46 mg) was added to the solution under ice cooling. The mixture was stirred at 80° C. for 2 hr. Water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using methanol-chloroform to give the title compound (37 mg, yield 28%).

Workup

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

Sources & evidence

ORD record
ord-2d1eaa91f6d749099635002c3c4a8fe6
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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