Water → 3-Methylpyrazine-2-carboxylic acid

HRID 1685042Notes

Reaction equation

HRID 1685042 reaction equation
[CH3:1][C:2]1[C:3]([CH3:8])=[N:4][CH:5]=[CH:6][N:7]=1.[O-:9][Mn](=O)(=O)=O.[K+].[OH2:15]>>[CH3:1][C:2]1[C:3]([C:8]([OH:9])=[O:15])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

4

Reactant 3

HCID 962Water2×HCID 222012,3-DimethylpyrazineHCID 516875Potassium Permanganate

Product 1

HCID 131534683-Methylpyrazine-2-carboxylic acidYield 30%

Procedure

A solution of dimethylpyrazine (25 g, 231 mmol) in water (250 mL) was heated at 70° C. and a solution of KMnO4 (82.2 g, 520 mmol) in water was added at such a rate to maintain the temperature between 70 and 75° C. The mixture was stirred until the purple color vanished and was filtered over Celite. The aqueous solution was extracted with EtOAc (6×800 mL), dried over Na2SO4 and concentrated in vacuo. The residue was titrated with TBME to afford 3-methylpyrazine-2-carboxylic acid (9.3 g, 67 mmol) as a white solid in 30% yield.

Workup

  1. temperatureto maintain the temperature between 70 and 75° C
  2. filtrationwas filtered over Celite
  3. extractionThe aqueous solution was extracted with EtOAc (6×800 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a817abe3d3b4e1ea69715862405b4e5
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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