4-Chloro-6,7-dimethoxyquinoline → 6,7-Dimethoxy-4-(quinolin-2-ylsulfanyl)-quinoline

HRID 229027Notes

Reaction equation

HRID 229027 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[SH:11].Cl[C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][CH:14]=1>C(#N)C>[CH3:24][O:23][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][C:19]=1[O:25][CH3:26])[N:16]=[CH:15][CH:14]=[C:13]2[S:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1

Participants

4

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 178418736HCID 178418736, compound

Product 1

HCID 230783196,7-Dimethoxy-4-(quinolin-2-ylsulfanyl)-quinolineYield 10%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Quinolinethiol (87 mg) and 4-chloro-6,7-dimethoxyquinoline (100 mg) were suspended in acetonitrile (3 ml), and the suspension was stirred at room temperature overnight. The solvent was removed by distillation under the reduced pressure. Water was added to the residue, and the mixture was neutralized with sodium hydrogencarbonate and was then extracted with chloroform. The chloroform layer was washed with water and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-chloroform to give the title compound (15 mg, yield 10%).

Workup

  1. customThe solvent was removed by distillation under the reduced pressure
  2. additionWater was added to the residue
  3. extractionwas then extracted with chloroform
  4. washThe chloroform layer was washed with water and saturated brine
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-88a8020c274944bfa8f874a75297eb2c
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

Loading…