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

HRID 1980411Notes

Reaction equation

HRID 1980411 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 hydrocholoric 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. concentrationwith concentrated hydrocholoric acid
  11. customThe solid which separated
  12. extractionwas extracted with ether
  13. extractionThe ether extract
  14. customwas dried
  15. customevaporated

Sources & evidence

ORD record
ord-a2c3067cdd27441fb131c52705d8b351
Source dataset
uspto-grants-1985_04
Patent number
US04508907

Reaction notes

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