Acetone → 5-Bromo-4-methylpyridine-2-carboxylic acid

HRID 1908797Notes

Reaction equation

HRID 1908797 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[CH:4]C(C=C)=[N:6][CH:7]=1.[O-:11][Mn](=O)(=O)=O.[K+].C[C:18]([CH3:20])=[O:19]>O>[Br:1][C:2]1[C:3]([CH3:10])=[CH:4][C:20]([C:18]([OH:11])=[O:19])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 516875Potassium PermanganateHCID 582004495-Bromo-4-methyl-2-vinylpyridine

Product 1

HCID 457900315-Bromo-4-methylpyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5-bromo-4-methyl-2-vinyl-pyridine (7.04 g, 35.5 mmol) in acetone (280 mL) and water (280 mL), KMnO4 (28.81 g, 71.1 mmol) is added. The dark mixture is stirred at rt for 3 days before it is filtered over a glass-filter pad. The colourless filtrate is evaporated to give crude 5-bromo-4-methyl-pyridine-2-carboxylic acid (10.9 g, as potassium salt) as a white solid; LC-MS: tR=0.64 min, [M+1]+=215.90.

Workup

  1. filtrationis filtered over a glass-filter pad
  2. customThe colourless filtrate is evaporated

Sources & evidence

ORD record
ord-c972bc0a4b804d29b15f8accd67390b7
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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