Water → 2-Bromoisonicotinic acid

HRID 1434704Notes

Reaction equation

HRID 1434704 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[Mn]([O-])(=O)(=O)=[O:10].[K+].[OH2:15]>>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][N:3]=1)[C:8]([OH:10])=[O:15]

Participants

4

Reactant 3

HCID 962WaterHCID 516875Potassium Permanganate2×HCID 27340872-Bromo-4-methylpyridine

Product 1

HCID 2227012-Bromoisonicotinic acid

Procedure

160 g (0.93 mol) of 2-bromo-4-methyl-pyridine is added in drops to 152 g (0.96 mol) of potassium permanganate in 4 l of water. Then, it is stirred under reflux for one hour before 152 g (0.96 mol) of potassium permanganate is added once more. After two additional hours of stirring under reflux, it is suctioned off in a hot state over Celite and washed with water. The aqueous phase is shaken out three times with dichloromethane. The aqueous phase is concentrated by evaporation to one-half its original volume, and the pH is set at 2 with concentrated hydrochloric acid. The precipitated solid is suctioned off and dried at 70° C. in a vacuum. 56.5 g of white solid product accumulates.

Workup

  1. additionis added once more
  2. stirringAfter two additional hours of stirring
  3. temperatureunder reflux
  4. washwashed with water
  5. stirringThe aqueous phase is shaken out three times with dichloromethane
  6. concentrationThe aqueous phase is concentrated by evaporation to one-half its original volume
  7. customdried at 70° C. in a vacuum

Sources & evidence

ORD record
ord-a9807820e9a14447b3bf47eef9dfe456
Source dataset
uspto-grants-2009_11
Patent number
US07615565B2

Reaction notes

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