Ethanol → Ethyl 2-(6,7-dimethoxy-quinolin-4-ylsulfanyl)-5-fluoro-benzoate

HRID 229026

Reaktionsgleichung

Reaktionsgleichung von HRID 229026
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[S:15][C:16]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:17]=1[C:18]([OH:20])=[O:19].S(Cl)(Cl)=O.[CH2:30](O)[CH3:31]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[S:15][C:16]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:17]=1[C:18]([O:20][CH2:30][CH3:31])=[O:19]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 230783772-(6,7-Dimethoxy-quinolin-4-ylsulfanyl)-5-fluoro-benzoic acid

Produkt 1

HCID 23078322Ethyl 2-(6,7-dimethoxy-quinolin-4-ylsulfanyl)-5-fluoro-benzoateAusbeute 84 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-(6,7-Dimethoxy-quinolin-4-ylsulfanyl)-5-fluoro-benzoic acid (76 mg) was suspended in ethanol (387 mg), and the suspension was cooled at 0° C. Thionyl chloride (50 mg) was gradually added dropwise thereto, and the mixture was then heated under reflux for 20 min. The solvent was removed by distillation under the reduced pressure, water was added to the residue, and the mixture was neutralized with a 20% aqueous sodium hydroxide solution and was then extracted with ethyl acetate. Next, the ethyl acetate layer was washed with water and saturated brine and 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 acetone-hexane to give the title compound (68 mg, 84%).

Aufarbeitung

  1. temperaturethe mixture was then heated
  2. temperatureunder reflux for 20 min
  3. customThe solvent was removed by distillation under the reduced pressure, water
  4. additionwas added to the residue
  5. extractionwas then extracted with ethyl acetate
  6. washNext, the ethyl acetate layer was washed with water and saturated brine
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ab1cd4f2ce044492810a09c0dc77ac37
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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