Hydrogen Peroxide → HCID 9839135, compound

HRID 1585570Notes

Reaction equation

HRID 1585570 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]2[C:18]#[N:19])=[O:7])=[CH:4][CH:3]=1.C(=O)(O)[O-:23].[Na+].OO>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][CH:9]2[C:18]([NH2:19])=[O:23])=[O:7])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 21219138HCID 21219138, compound

Product 1

HCID 9839135HCID 9839135, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-(4-Fluorobenzoyl)-1,2-dihydro-quinoline-2-carbonitrile (24.0 g) was dissolved in acetone (500 mL). Solid sodium bicarbonate (15 g) was added. The mixture was stirred for 10 minutes. 30% Hydrogen peroxide solution (300 mL of a 30% solution) was added drop-wise. Stirring was continued for 30 minutes. The mixture was then warmed slowly until a solution formed, then stirred at ambient temperature for 2 hours. The acetone was evaporated under vacuum. The aqueous residue was diluted with water (100 mL), and acidified with 1N HCl. The mixture was extracted with ethyl acetate (500 mL). The organic extract was washed with water (300 mL), dried over anhydrous sodium sulfate, then concentrated. Hexane was added to the precipitation point. The solid was collected and dried to give the title compound as a white solid, m. p. 149-151° C.

Workup

  1. stirringStirring
  2. waitwas continued for 30 minutes
  3. temperatureThe mixture was then warmed slowly until a solution
  4. customformed
  5. stirringstirred at ambient temperature for 2 hours
  6. customThe acetone was evaporated under vacuum
  7. additionThe aqueous residue was diluted with water (100 mL)
  8. extractionThe mixture was extracted with ethyl acetate (500 mL)
  9. extractionThe organic extract
  10. washwas washed with water (300 mL)
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated
  13. additionHexane was added to the precipitation point
  14. customThe solid was collected
  15. customdried

Sources & evidence

ORD record
ord-ed4ccaca349c476eac6f55b3bc8a1494
Source dataset
uspto-grants-1999_08
Patent number
US05939435

Reaction notes

Loading…