Water → 2-Bromopyridine-3-carboxylic acid

HRID 400570Notes

Reaction equation

HRID 400570 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Mn]([O-])(=O)(=O)=[O:10].[K+].[OH2:15]>>[Br:1][C:2]1[N:3]=[CH:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:15]

Participants

4

Reactant 3

HCID 962WaterHCID 2208322-Bromo-3-methylpyridineHCID 516875Potassium Permanganate

Product 1

HCID 2332622-Bromopyridine-3-carboxylic acidYield 62%

Procedure

2-bromo-3-methylpyridine (25.0 mL, 213 mmol) was added to a solution of potassium permanganate (87.7 g, 555 mmol) in 800 mL of water and the mixture was stirred under reflux. After 5 hours, 600 mL of water was distilled off and the remaining suspension was filtered. The residue was washed with two 50 mL portions of hot water and the combined filtrates were acidified with concentrated HCl. The white precipitate was filtered and dried in a vacuum oven to give 26.8 g of 2-bromonicotinic acid (62% yield).

Workup

  1. temperatureunder reflux
  2. distillation600 mL of water was distilled off
  3. filtrationthe remaining suspension was filtered
  4. washThe residue was washed with two 50 mL portions of hot water
  5. filtrationThe white precipitate was filtered
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-4fcc23852eb44d22825e6ee78e74123c
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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