Phosphorus oxychloride → 3-Butyryl-6-benzyloxy-4-chloro-8-methoxy quinoline

HRID 1885193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1885193
[C:1]([C:6]1[C:15](=O)[C:14]2[C:9](=[C:10]([O:26][CH3:27])[CH:11]=[C:12]([O:17][C:18](=O)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:13]=2)[NH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:30])=O>>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:30])=[CH:13][C:12]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[CH:11][C:10]=2[O:26][CH3:27])(=[O:5])[CH2:2][CH2:3][CH3:4]

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 104065273-butyryl-6-benzoyloxy-8-methoxy-4(1H)-quinolone

Produkt 1

HCID 198802873-Butyryl-6-benzyloxy-4-chloro-8-methoxy quinoline

Versuchsvorschrift

3-Butyryl-6-benzoyloxy-8-methoxy-4(1H)-quinolone (18.0 g) was heated under reflux in phosphorus oxychloride (100 ml) for 40 minutes. The solvent was evaporated and the residue dissolved in dichloromethane and poured into a vigorously stirred mixture of ice and sodium hydrogen carbonate solution. The organic phase was washed with sodium hydrogen carbonate solution, dried, filtered and evaporated to give 3-butyryl-6-benzyloxy-4-chloro-8-methoxy quinoline as a brown oil (25 g).

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. additionpoured into a vigorously stirred mixture of ice and sodium hydrogen carbonate solution
  4. washThe organic phase was washed with sodium hydrogen carbonate solution
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ffeb59053f484f92991a4bee1897905b
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05143920

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