Hydrogen Peroxide → 2,6-Dichloropyridine N-Oxide

HRID 1190810Notes

Reaction equation

HRID 1190810 reaction equation
FC(F)(F)C(O)=[O:4].[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[N:10]=1.OO>O>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[N+:10]=1[O-:4]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 169892,6-Dichloropyridine

Product 1

HCID 8176732,6-Dichloropyridine N-OxideYield 87.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After the reaction solution of trifluoroacetic acid (485 mL, 6.3 mol), 2,6-dichloropyridine (48 g, 324 mmol) and 35% hydrogen peroxide (85.0 mL, 971 mmol) was stirred for 6.5 h under the condition of reflux, it was cooled to room temperature. The reaction solution was poured into beaker contained 2.4 L water, and cooled overnight at 0° C. The solid (unreacted 2,6-dichloropyridine) was removed through a suction filtration. The filtrate was concentrated, to which 500 mL chloroform was added, and potassium carbonate was added until no gas was produced. It was filtrated. The filtrate was concentrated under vacuum to afford 46.6 g light yellow solid, 87.6%.

Workup

  1. temperatureof reflux
  2. additionThe reaction solution was poured into beaker
  3. temperaturecooled overnight at 0° C
  4. customThe solid (unreacted 2,6-dichloropyridine) was removed through a suction filtration
  5. concentrationThe filtrate was concentrated, to which 500 mL chloroform
  6. additionwas added
  7. additionpotassium carbonate was added until no gas
  8. customwas produced
  9. filtrationIt was filtrated
  10. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-4afa70ff02b64439b456ee9909f5fb4e
Source dataset
uspto-grants-2014_03
Patent number
US08680089B2

Reaction notes

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