Potassium Permanganate → 2-Bromoisonicotinic acid

HRID 1174507Notes

Reaction equation

HRID 1174507 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[O-:9][Mn](=O)(=O)=O.[K+].N1C=CC=CC=1.[OH2:21]>O>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][N:3]=1)[C:8]([OH:9])=[O:21]

Participants

5

Reactant 3

HCID 516875Potassium Permanganate2×HCID 27340872-Bromo-4-methylpyridineHCID 66926435Pyridine water

Product 1

HCID 2227012-Bromoisonicotinic acidYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-bromo-4-picoline (300 g, 1.74 mol) in pyridine/water (1 L each) at 95° C. was added KMnO4 (200 g) dissolved in water (IL). Further, added KMnO4 (2 Kg) in portions (app. 20 mg each time) over a period of 4 days. The reaction mixture was cooled to RT and filtered off the solid MnO2. The filtrate was evaporated completely under reduce pressure and acidified with 6N HCl. The solid product obtained was filtered, washed with water and dried to give 2-bromoisonicotinic acid (166 g, 47%).

Workup

  1. filtrationfiltered off the solid MnO2
  2. customThe filtrate was evaporated completely
  3. customThe solid product obtained
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-1e632686e53f4e67ac0f704a64ff11f6
Source dataset
uspto-grants-2010_11
Patent number
US07838522B2

Reaction notes

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