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

HRID 229025

反応式

HRID 229025 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-a4a7f85be8454dc59ed6a9c1a3eeba17
出典データセット
uspto-grants-2009_07
特許番号
US07560558B2

関連ノート

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