4-Hydroxyquinoline → Quinoline

HRID 1534471

Reaktionsgleichung

Reaktionsgleichung von HRID 1534471
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH:3]=[CH:2]1>P(Cl)(Cl)(Cl)=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Komponenten

3

Edukt 1

HCID 691414-Hydroxyquinoline

Produkt 1

HCID 7047QuinolineAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24813Phosphorus oxychlorideLösungsmittel

Versuchsvorschrift

3-butyryl-6-benzoyloxymethyl)-4(1H)-quinolone (30 g) was heated under reflux in phosphorus oxychloride (200 ml) for 30 minutes. The solvent was evaporated and the residue partitioned between dichloromethane and ammonia solution. The organic layer was washed successively with sodium hydrogen carbonate solution and 50% brine. Dried anhyd. MgSO4), filtered and evaporated to an oily solid which crystallized on trituration with petroleum ether to give 3-butyryl-4-chloro-6-benzyloxymethyl)quinoline (21.2 g, 67%), m.p. 85° C.-6° C.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe residue partitioned between dichloromethane and ammonia solution
  3. washThe organic layer was washed successively with sodium hydrogen carbonate solution and 50% brine
  4. customDried
  5. filtrationMgSO4), filtered
  6. customevaporated to an oily solid which
  7. customcrystallized on trituration with petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-14c173a9bff4469eb6fc04397d1b6174
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05089504

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