Methanol → 2-Pyrazinecarboxylic acid, 5-methyl-, methyl ester

HRID 11850

Reaction equation

HRID 11850 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.ClCl.[CH3:13]O>>[CH3:13][O:9][C:8]([C:5]1[CH:4]=[N:3][C:2]([CH3:1])=[CH:7][N:6]=1)=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 24526ChlorineHCID 1228315-Methyl-2-pyrazinecarboxylic acid

Product 1

HCID 4650652-Pyrazinecarboxylic acid, 5-methyl-, methyl ester

Procedure

Commercially available 5-methylpyrazine 2-carboxylic acid (2.05 g) was dissolved in methanol (0.6 ml) and chlorine gas was blown into the solution for 5 minutes. After four hours, the reaction solution was concentrated and 1 mol/l aqueous solution of sodium hydroxide was added, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The resulting solid was recrystallized from hexane/ethyl acetate. The deposited crystals were collected by filtration and dried under reduced pressure to obtain the title compound (1.44 g) as light brown scale-like crystals.

Workup

  1. concentrationthe reaction solution was concentrated
  2. addition1 mol/l aqueous solution of sodium hydroxide was added
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting solid was recrystallized from hexane/ethyl acetate
  8. filtrationThe deposited crystals were collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-1a9513f02e8c489b998c3f5654a17c95
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Linked notes

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