Acetone → 5-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-one

HRID 1380143Notes

Reaction equation

HRID 1380143 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:15])[NH:9]2)(=[O:3])[CH3:2].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CC(C)=O.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]([C:4]1[CH:13]=[CH:12][C:11]([O:14][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:15])[NH:9]2)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 119838955-Acetyl-8-hydroxy-2(1H)-quinolinone

Product 1

HCID 133754445-Acetyl-8-(benzyloxy)-1,2-dihydroquinolin-2-oneYield 46.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15.23 g of 5-acetyl-8-hydroxycarbostyril and 15.7 g of benzyl chloride are added to a mixture of 200 ml of acetone and 90 ml of water, and 10.35 g of potassium carbonate are added thereto. The mixture is refluxed for 12 hours under stirring. Then, the mixture is evaporated under reduced pressure to remove acetone, and the residue is extracted with chloroform. The extract is washed with water, dried and evaporated under reduced pressure to remove chloroform. The residue is recrystallized from a mixture of ethyl acetate and n-hexane. 10.14 g of 5-acetyl-8-benzyloxycarbostyril are obtained as prisms. 1.58 g of said product are further recovered from the mother liquor.

Workup

  1. additionare added
  2. temperatureThe mixture is refluxed for 12 hours
  3. customThen, the mixture is evaporated under reduced pressure
  4. customto remove acetone
  5. extractionthe residue is extracted with chloroform
  6. washThe extract is washed with water
  7. customdried
  8. customevaporated under reduced pressure
  9. customto remove chloroform
  10. customThe residue is recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-7078f5ed54394ea484a383d3be141ec4
Source dataset
uspto-grants-1986_04
Patent number
US04579854

Reaction notes

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