Acetic Acid → 5-(Methylsulfonyl)-2-nitropyridine

HRID 1411526Notes

Reaction equation

HRID 1411526 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[N:7][CH:8]=1.OO.[OH2:14].C(O)(=[O:17])C>>[CH3:1][S:2]([C:3]1[CH:4]=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[N:7][CH:8]=1)(=[O:17])=[O:14]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 220361825-(Methylthio)-2-nitropyridine

Product 1

HCID 203555045-(Methylsulfonyl)-2-nitropyridineYield 86%

Conditions

Temperature
25 °C

Procedure

To a mixture of 117a (260 mg, 0.5 mmol) in acetic acid (15 mL) was added H2O2 (aq. 30%) (7.5 mL) and the reaction mixture was stirred overnight at 25° C. The reaction solution was poured into water and extracted with EtOAC and concentrated to a pale yellow liquid, purified by silica gel with (EtOAC/PE:1:3) to give 117b (2 g, 86%). MS: [M+H]+ 203.

Workup

  1. extractionextracted with EtOAC
  2. concentrationconcentrated to a pale yellow liquid
  3. custompurified by silica gel with (EtOAC/PE:1:3)

Sources & evidence

ORD record
ord-5bfa4819fb89472395e730b6df98c7e2
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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