Allyl bromide → HCID 19068025, compound

HRID 1957538Notes

Reaction equation

HRID 1957538 reaction equation
[CH2:1]([C:4]1C=C2C(=CC=1O)NC(=O)CC2)[CH:2]=C.[CH2:16]([C:19]1[C:20]([OH:30])=[CH:21][CH:22]=[C:23]2[C:28]=1[NH:27][C:26](=[O:29])[CH2:25][CH2:24]2)[CH:17]=[CH2:18].C(Br)C=C>CO.[OH-].[K+]>[CH2:16]([C:19]1[C:20]([O:30][CH2:4][CH:1]=[CH2:2])=[CH:21][CH:22]=[C:23]2[C:28]=1[NH:27][C:26](=[O:29])[CH2:25][CH2:24]2)[CH:17]=[CH2:18]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 19067931HCID 19067931, compoundHCID 19068044HCID 19068044, compound

Product 1

HCID 19068025HCID 19068025, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

6.1 Grams of the mixture of 6-allyl-3,4-dihydro-7-hydroxy-2(1H)-quinolinone and 8-allyl-3,4-dihydro-7-hydroxy-2(1H)-quinolinone obtained in Example 8 was dissolved in 200 ml of methanol containing 1.8 g of potassium hydroxide. Under stirring, 3 ml of allyl bromide was added thereto at room temperature. The reaction mixture was stirred at room temperature for 4 hours, and further stirred at 60° C. for 1 hour. After the reaction was finished, the reaction mixture was concentrated under reduced pressure, next 200 ml of water was added and stirred vigorously, then extracted with 500 ml of ethyl acetate. The extract was washed with water and an aqueous solution saturated with sodium chloride, and dried with anhydrous magnesium sulfate. The magnesium sulfate was removed by filtration, and the filtrate was concentrated to dryness. This mixture was subjected to purification by means of a flush column chromatography by using methylene chloride-methanol (100:1). The first eluted portion was collected and concentrated under reduced pressure, there was obtained 4.4 g (60%) of 8-allyl-7-allyloxy-3,4-dihydro-2(1H)-quinolinone. Colorless needle-like crystals (recrystallized from ethyl acetate-n-hexane). Melting point: 119°-121° C.

Workup

  1. customat room temperature
  2. stirringThe reaction mixture was stirred at room temperature for 4 hours
  3. stirringfurther stirred at 60° C. for 1 hour
  4. concentrationthe reaction mixture was concentrated under reduced pressure, next 200 ml of water
  5. additionwas added
  6. stirringstirred vigorously
  7. extractionextracted with 500 ml of ethyl acetate
  8. washThe extract was washed with water
  9. dry with materialan aqueous solution saturated with sodium chloride, and dried with anhydrous magnesium sulfate
  10. customThe magnesium sulfate was removed by filtration
  11. concentrationthe filtrate was concentrated to dryness
  12. customThis mixture was subjected to purification by means of a flush column chromatography
  13. customThe first eluted portion was collected
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-101785dbf3ad4c01beade79a8ccef391
Source dataset
uspto-grants-1998_07
Patent number
US05786367

Reaction notes

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