Thionyl Chloride → Methyl 4-chloro-7-methoxyquinoline-6-carboxylate

HRID 393665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 393665
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=O)[CH:8]=[CH:9][NH:10]2)=[CH:5][C:4]=1[C:14]([O:16][CH3:17])=[O:15].S(Cl)([Cl:20])=O>CN(C=O)C>[Cl:20][C:7]1[C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[C:4]([C:14]([O:16][CH3:17])=[O:15])[CH:5]=2)[N:10]=[CH:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 22646623Methyl 1,4-dihydro-7-methoxy-4-oxo-6-quinolinecarboxylate

Produkt 1

HCID 22646520Methyl 4-chloro-7-methoxyquinoline-6-carboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 7-methoxy-6-methoxycarbonyl-1,4-dihydroquinolin-4-one (5.4 g, 23 mmol), DMF (0.4 ml) and thionyl chloride (75 ml) was heated at reflux for 2 hours and then stirred at ambient temperature for a further 2 hours. The excess thionyl chloride was removed by evaporation and by azeotroping with toluene. The residue was suspended in methylene chloride and washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, dried by passing through phase separating paper and the solvent was removed by evaporation. The residue was suspended in ether, collected by filtration, washed with hexane and dried to give 4-chloro-7-methoxy-6-methoxycarbonylquinoline (4.06 g, 70%) as an orange solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe excess thionyl chloride was removed by evaporation
  4. customby azeotroping with toluene
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution
  6. customThe organic layer was separated
  7. customdried
  8. customseparating paper
  9. customthe solvent was removed by evaporation
  10. filtrationcollected by filtration
  11. washwashed with hexane
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5980cf10db914ccab7897e125208a955
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809097B1

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