Hydrochloric Acid → 5-(Chloroacetyl)-8-hydroxy-2(1H)-quinolinone

HRID 2397553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2397553
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2.[Cl:13][CH2:14][C:15](Cl)=[O:16].[Cl-].[Al+3].[Cl-].[Cl-].Cl>[N+](C1C=CC=CC=1)([O-])=O>[Cl:13][CH2:14][C:15]([C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:12])[NH:10]2)=[O:16]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 972508-hydroxyquinolin-2(1H)-oneHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 132602995-(Chloroacetyl)-8-hydroxy-2(1H)-quinolinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7416NitrobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

27 g of 8-hydroxycarbostyril (VII) and 37 ml of chloroacetyl chloride were dissolved in 250 ml of nitrobenzene, and to the resulting solution was added 85 g of aluminum chloride followed by stirring at 70° C. for 20 hours. 500 ml of 10% aqueous hydrochloric acid was added to the reaction mixture and the nitrobenzene was removed by steam distillation. After cooling the mixture, the precipitated crystals were collected by filtration which were then washed with 300 ml of hot water. Recrystallization from methanol gave 14.0 g of 5-chloroacetyl-8-hydroxycarbostyril (IV) having a melting point of 285°-287° C. (with decomposition) as pale yellow crystals.

Aufarbeitung

  1. customthe nitrobenzene was removed by steam distillation
  2. temperatureAfter cooling the mixture
  3. filtrationthe precipitated crystals were collected by filtration which
  4. washwere then washed with 300 ml of hot water
  5. customRecrystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-06b76146392547ac868d14320262e45e
Quelldatensatz
uspto-grants-1977_05
Patentnummer
US04022776

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