Acetic Acid → 1-(1-Oxido-3-pyridinyl)ethanone

HRID 1451145Notes

Reaction equation

HRID 1451145 reaction equation
OO.C(O)(=[O:5])C.[C:7]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)(=[O:9])[CH3:8].C([O-])([O-])=O.[K+].[K+]>CC(O)C>[C:7]([C:10]1[CH:11]=[N+:12]([O-:5])[CH:13]=[CH:14][CH:15]=1)(=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 95893-AcetylpyridineHCID 11430Potassium Carbonate

Product 1

HCID 1233381-(1-Oxido-3-pyridinyl)ethanone

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Hydrogen peroxide (20.9 ml, 0.61453 moles, Baker) and acetic acid (125 ml, Baker) were combined and stirred at room temperature (RT). The 3-acetylpyridine (50 ml, 0.40984 moles, Aldrich), distilled prior to use (94° C., 2.00 mm Hg), was added and then, the reaction mixture was stirred overnight (O/N) at 95° C. Next, the reaction mixture was cooled to RT and then, neutralized with saturated K2CO3 (400 ml). Then, 5 g of KSO3 was added to destroy the remaining hydrogen peroxide. Next, methanol (750 ml) was added and the resultant cloudy solution was filtered. The filtrate was then evaporated to dryness using a rotary evaporator. The semi-solid was extracted repeatedly with hot CH2Cl2 (4×500 ml) and combined. Next, the solvent was removed leaving approximately 44 g of a crude, pale yellow solid. The crude solid was dissolved in hot 2-propanol (150 ml) and stirred until cool in an icebath. The white solid which precipitated was collected, washed with 2-propanol (100 ml) and dried in a vacuum dessicator O/N at 50° C. The air-dried weight was 41 g. HPLC analysis of the recrystallized sample (m.p. 146°-147° C.) showed a single principal peak 96% by area.

Workup

  1. custom(94° C., 2.00 mm Hg)
  2. additionwas added
  3. stirringthe reaction mixture was stirred overnight (O/N) at 95° C
  4. temperatureNext, the reaction mixture was cooled to RT
  5. customto destroy the remaining hydrogen peroxide
  6. additionNext, methanol (750 ml) was added
  7. filtrationthe resultant cloudy solution was filtered
  8. customThe filtrate was then evaporated to dryness
  9. customa rotary evaporator
  10. extractionThe semi-solid was extracted repeatedly with hot CH2Cl2 (4×500 ml)
  11. customNext, the solvent was removed
  12. customleaving approximately 44 g of a crude, pale yellow solid
  13. stirringstirred
  14. temperatureuntil cool in an icebath
  15. customThe white solid which precipitated
  16. customwas collected
  17. washwashed with 2-propanol (100 ml)
  18. customdried in a vacuum dessicator O/N at 50° C

Sources & evidence

ORD record
ord-33b0c719d41b46b1b2cf5285fb3d7b75
Source dataset
uspto-grants-1997_02
Patent number
US05604079

Reaction notes

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