Water → 5-Bromo-6-chloropyridine-3-carboxylic acid

HRID 1584064Notes

Reaction equation

HRID 1584064 reaction equation
[Br:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[Mn]([O-])(=O)(=O)=[O:11].[K+].[OH2:16]>>[Br:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[C:6]([C:8]([OH:11])=[O:16])[CH:7]=1

Participants

4

Reactant 3

HCID 962WaterHCID 2854373-Bromo-2-chloro-5-methylpyridineHCID 516875Potassium Permanganate2×

Product 1

HCID 2854335-Bromo-6-chloropyridine-3-carboxylic acid

Procedure

3-Bromo-2-chloro-5-methylpyridine (30 g) in water (650 ml) containing potassium permanganate (60 g) was stirred and heated under reflux for 3 hours. Further potassium permanganate (20 g) was then added and the mixture heated and stirred for another 21/2 hours. The mixture was steam-distilled to remove unchanged starting material, and then filtered while hot. The residue was washed with hot water. The filtrate and washings were cooled and acidified with concentrated hydrochloric acid. The solid which separated was extracted with ether. The ether extract was dried and evaporated to give 3-bromo-2-chloropyridine-5-carboxylic acid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. temperaturethe mixture heated
  4. stirringstirred for another 21/2 hours
  5. distillationThe mixture was steam-distilled
  6. customto remove unchanged
  7. filtrationfiltered while hot
  8. washThe residue was washed with hot water
  9. temperatureThe filtrate and washings were cooled
  10. customThe solid which separated
  11. extractionwas extracted with ether
  12. extractionThe ether extract
  13. customwas dried
  14. customevaporated

Sources & evidence

ORD record
ord-1383b64d824b48b098bc1874593e59c2
Source dataset
uspto-grants-1985_11
Patent number
US04555575

Reaction notes

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