Acetone → 2-(methylsulfonyl)-5-nitropyridine

HRID 1860594Notes

Reaction equation

HRID 1860594 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7](SC)=[CH:8][CH:9]=1)([O-:3])=[O:2].[S:12](=[O:16])(=O)(O)[OH:13].[Mn]([O-])(=O)(=O)=O.[K+].[CH3:23]C(C)=O>>[N+:1]([C:4]1[CH:5]=[N:6][C:7]([S:12]([CH3:23])(=[O:16])=[O:13])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 516875Potassium PermanganateHCID 44393132-(Methylthio)-5-nitropyridine

Product 1

HCID 12115522-(methylsulfonyl)-5-nitropyridineYield 70%

Procedure

3-Nitro-6-(methylthio)pyridine (22.0 g, 129.3 mmol) was dissolved in acetone (140 mL). Sulfuric acid (2N, 230 mL) was then added dropwise to above solution to form a slurry. Potassium permanganate (KMnO4) (26.5 g, 168.1 mmol, dissolved in 500 mL of H2O) was added to the above mixture dropwise. The mixture that resulted was stirred at room temperature overnight. The solid was filtered and stirred with a warm mixture of ethanol/methanol (10/1). The insoluble salt was filtered, the filtrate was concentrated to provide a pale yellow solid. The crude product was recrystallized from ethanol to furnish the title compound (17.8 g, 70%).

Workup

  1. customto form a slurry
  2. customThe mixture that resulted
  3. filtrationThe solid was filtered
  4. stirringstirred with a warm mixture of ethanol/methanol (10/1)
  5. filtrationThe insoluble salt was filtered
  6. concentrationthe filtrate was concentrated
  7. customto provide a pale yellow solid
  8. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-b07859c163f740028de2414842b72912
Source dataset
uspto-grants-2003_03
Patent number
US06531492B1

Reaction notes

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