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

HRID 1957533Notes

Reaction equation

HRID 1957533 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 190680326-(allyloxy)-3,4-dihydroquinolin-2(1H)-oneYield 68.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-029a50753efa4c9d9d49860005c7347b
Source dataset
uspto-grants-1998_07
Patent number
US05786367

Reaction notes

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