4-Chloro-6,7-dimethoxyquinoline → 2-(6,7-Dimethoxy-quinolin-4-ylsulfanyl)-5-fluoro-benzoic acid

HRID 229025Notes

Reaction equation

HRID 229025 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([SH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].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:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 27833715-Fluoro-2-mercaptobenzoic acid

Product 1

HCID 230783772-(6,7-Dimethoxy-quinolin-4-ylsulfanyl)-5-fluoro-benzoic acidYield 31.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Fluoro-2-mercaptobenzoic acid (278 mg) and 4-chloro-6,7-dimethoxyquinoline (300 mg) were suspended in acetonitrile (6 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, 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 chloroform-methanol to give 2-(6,7-dimethoxy-quinolin-4-ylsulfanyl)-5-fluoro-benzoic acid (152 mg, yield 31%).

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-a4a7f85be8454dc59ed6a9c1a3eeba17
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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