Water → 2-(methylsulfonyl)-5-nitropyridine

HRID 2387290Notes

Reaction equation

HRID 2387290 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][N:4]=1.I([O-])(=O)(=O)=[O:13].[Na+].[OH2:18]>CC#N.[Ru](Cl)(Cl)Cl>[CH3:1][S:2]([C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][N:4]=1)(=[O:13])=[O:18]

Participants

6

Reactant 3

HCID 962WaterHCID 44393132-(Methylthio)-5-nitropyridineHCID 23667635Sodium periodate

Product 1

HCID 12115522-(methylsulfonyl)-5-nitropyridineYield 94%

Reagents, catalysts & solvents 2

HCID 61850Ruthenium trichlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of 620 mg (3.64 mmol) of 2-methylsulfanyl-5-nitropyridine in 33 mL of MeCN and 9 mL of water was added 2.34 g (10.9 mmol) of sodium periodate followed by the addition of 15 mg (0.07 mmol) of ruthenium (III) chloride and the reaction was stirred at room temperature for 16 hours. The solids were filtered and the filtrate was diluted with 50 mL of water, extracted with 150 mL of ethyl acetate, dried over magnesium sulfate, filtered, and concentrated in vacuo. The grey solid was purified by filtration through a silica column with DCM to afford 693 mg (94%) of 2-methanesulfonyl-5-nitropyridine.

Workup

  1. filtrationThe solids were filtered
  2. additionthe filtrate was diluted with 50 mL of water
  3. extractionextracted with 150 mL of ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. filtrationThe grey solid was purified by filtration through a silica column with DCM

Sources & evidence

ORD record
ord-c235f2b60b3c44f9bac4defaa83593cb
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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