Hydrochloric Acid → HCID 23287785, compound

HRID 367029Notes

Reaction equation

HRID 367029 reaction equation
[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:16])[NH:10]2)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[CH:24]=[CH2:25].Cl>CN(C=O)C.O>[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH2:25][CH:24]=[CH2:23])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:16])[NH:10]2)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 23287788HCID 23287788, compound

Product 1

HCID 23287785HCID 23287785, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

10 Grams of 5-acetoxy-8-hydroxy-2(1H)-quinolinone was dissolved in 100 ml of DMF, to this solution was added 14 g of potassium carbonate and 9 ml of allyl bromide, stirred at room temperature for 8 hours. Under ice-cooling and stirring conditions, the reaction mixture was acidified by adding hydrochloric acid, this mixture was diluted by adding 200 ml of water. The mixture was extracted with 500 ml of ethyl acetate, the extract was washed with water, dried over anhydrous magnesium sulfate, then concentrated to dryness under reduced pressure. The residue thus obtained was recrystallized from a mixed solvent of ethyl acetate-n-hexane, there was obtained 9.8 g of 5-acetoxy-8-allyloxy-2(1H)-quinolinone as pale yellow needle-like crystals.

Workup

  1. temperatureUnder ice-cooling
  2. stirringstirring conditions
  3. additionthis mixture was diluted
  4. extractionThe mixture was extracted with 500 ml of ethyl acetate
  5. washthe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe residue thus obtained
  9. customwas recrystallized from a mixed solvent of ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-afb65ec02aea4e38b9bf662f1d30d64b
Source dataset
uspto-grants-2000_10
Patent number
US06133264

Reaction notes

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