Hydrogen Peroxide → 2-Chloro-5-methylpyridin-1-ium-1-olate

HRID 271065

Reaction equation

HRID 271065 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[OH:9]O>C(O)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N+:3]=1[O-:9]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 5813932-Chloro-5-methyl-pyridine

Product 1

HCID 134316232-Chloro-5-methylpyridin-1-ium-1-olateYield 82%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-5-methylpyridine (10 mL) in 155 mL of glacial acetic acid was added 19 mL of 30% aqueous hydrogen peroxide. The mixture was stirred at 80° C. for 8 hours. The mixture was diluted with 100 mL of water and then concentrated in a vacuum. The residue was made strongly alkaline with anhydrous sodium carbonate and shaken with 200 mL of chloroform. The solids were removed via filtration, and the filtrate was dried over sodium sulfate, filtered and concentrated to give 10.8 g of the 2-chloro-5-methylpyridine-N-oxide (82%). Mass Spec. M+H=144.

Workup

  1. concentrationconcentrated in a vacuum
  2. stirringshaken with 200 mL of chloroform
  3. customThe solids were removed via filtration
  4. dry with materialthe filtrate was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c8e8c040bbd246b7bf3eebdc08915175
Source dataset
uspto-grants-2008_11
Patent number
US07452880B2

Linked notes

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