Allyl bromide → 6-(allyloxy)-3,4-dihydroquinolin-2(1H)-one

HRID 1957533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1957533
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[CH2:13](Br)[CH:14]=[CH2:15]>CO.[OH-].[K+]>[CH2:15]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2)[CH:14]=[CH2:13]

Komponenten

5

Edukt 2

HCID 7841Allyl bromideHCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinone

Produkt 1

HCID 190680326-(allyloxy)-3,4-dihydroquinolin-2(1H)-oneAusbeute 68,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 14797Potassium HydroxideLösungsmittel

Versuchsvorschrift

32.6 Grams of 3,4-dihydro-6-hydroxy-2(1H)-quinolinone was dissolved in 500 ml of methanol containing 12.6 g of potassium hydroxide. Under stirring this solution, 20 ml of allyl bromide was added thereto at room temperature. The reaction mixture was stirred at room temperature for 1 hour, and further stirred at 60° C. for 4 hours. After the reaction, the reaction mixture was concentrated to a half volume under reduced pressure, then 500 ml of water was added and stirred vigorously, the crystals precipitated were collected by filtration. The crystals were washed with water and small amount of diethyl ether in this order, and dried. Recrystallized from ethanol, 28 g (68.9%) of 6-allyloxy-3,4-dihydro-2(1H)-quinolinone was obtained. Colorless needle-like crystals (recrystallized from ethanol)

Aufarbeitung

  1. additionwas added
  2. customat room temperature
  3. stirringfurther stirred at 60° C. for 4 hours
  4. customAfter the reaction
  5. concentrationthe reaction mixture was concentrated to a half volume under reduced pressure
  6. addition500 ml of water was added
  7. stirringstirred vigorously
  8. customthe crystals precipitated
  9. filtrationwere collected by filtration
  10. washThe crystals were washed with water and small amount of diethyl ether in this order
  11. customdried
  12. customRecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-029a50753efa4c9d9d49860005c7347b
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05786367

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