Potassium Permanganate → N-(3-Fluoro-5,6,7,8-tetrahydro-4-methyl-8-oxo-1-naphthalenyl)acetamide

HRID 1458311Notes

Reaction equation

HRID 1458311 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[C:13]([F:15])[C:12]([CH3:16])=[C:11]2[C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10]2)(=[O:3])[CH3:2].C(=O)(O)[O-:18].[Na+].[Mn]([O-])(=O)(=O)=O.[K+].S([O-])(O)=O.[Na+]>CC(C)=O.C(Cl)(Cl)Cl>[C:1]([NH:4][C:5]1[CH:14]=[C:13]([F:15])[C:12]([CH3:16])=[C:11]2[C:6]=1[C:7](=[O:18])[CH2:8][CH2:9][CH2:10]2)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 516875Potassium Permanganate3×HCID 516892Sodium BicarbonateHCID 10799012N-(3-Fluoro-4-methyl-5,6,7,8-tetrahydro-1-naphthyl)acetamideHCID 23665763Sodium Bisulfite

Product 1

HCID 22449535N-(3-Fluoro-5,6,7,8-tetrahydro-4-methyl-8-oxo-1-naphthalenyl)acetamideYield 48.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

In acetone, 5.0 g of 5-acetylamino-7-fluoro-8 -methyl-1,2,3,4-tetrahydronaphthalene were suspended, followed by the addition of 2.3 g of sodium bicarbonate. To the resulting mixture, 13.9 g of potassium permanganate were added in portions over 3.5 hours at an internal temperature of 10° to 15° C. and the mixture was stirred at room temperature for one hour. To the resulting mixture, 0.8 g of potassium permanganate was added further, followed by stirring for 1.5 hours. After a 5% aqueous solution of sodium hydrogensulfite was added in a small amount and the complete disappearance of potassium permanganate was confirmed, manganese dioxide so precipitated was filtered out. The manganese dioxide was washed thoroughly with chloroform and the filtrate was removed under reduced pressure. The residue so obtained was dissolved in chloroform. The resulting solution was washed three times with a saturated aqueous solution of sodium bicarbonate and dried over potassium carbonate. The solvent was evaporated under reduced pressure. The residue so obtained was recrystallized from chloroform-diethyl ether, whereby 2.6 g of the title compound was obtained.

Workup

  1. stirringby stirring for 1.5 hours
  2. custommanganese dioxide so precipitated
  3. filtrationwas filtered out
  4. washThe manganese dioxide was washed thoroughly with chloroform
  5. customthe filtrate was removed under reduced pressure
  6. customThe residue so obtained
  7. washThe resulting solution was washed three times with a saturated aqueous solution of sodium bicarbonate
  8. dry with materialdried over potassium carbonate
  9. customThe solvent was evaporated under reduced pressure
  10. customThe residue so obtained
  11. customwas recrystallized from chloroform-diethyl ether

Sources & evidence

ORD record
ord-e6217c68235c4869adec952f5430d5e5
Source dataset
uspto-grants-1998_12
Patent number
US05849945

Reaction notes

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