Water → 5-Ethoxypyrazine-2-carboxylic acid

HRID 218014Notes

Reaction equation

HRID 218014 reaction equation
[OH-].[Na+].Cl[C:4]1[N:5]=[CH:6][C:7]([C:10]([O:12]C)=[O:11])=[N:8][CH:9]=1.[C:14](OCC)(=[O:16])[CH3:15].O>C(O)C>[CH2:14]([O:16][C:4]1[N:5]=[CH:6][C:7]([C:10]([OH:12])=[O:11])=[N:8][CH:9]=1)[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 406081Methyl 5-chloropyrazine-2-carboxylate

Product 1

HCID 574756925-Ethoxypyrazine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 5 N sodium hydroxide solution (2 mL) was added to a solution of methyl 5-chloropyrazine-2-carboxylate (150 mg) in ethanol (4 mL), and the mixture was stirred at room temperature for five hours. Ethyl acetate and water were added to the reaction solution, and the aqueous layer was separated. The aqueous layer was made acidic with concentrated hydrochloric acid. Brine and ethyl acetate were added to the mixture, and the organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate. The organic layer was concentrated to obtain the title compound (135 mg).

Workup

  1. customthe aqueous layer was separated
  2. additionBrine and ethyl acetate were added to the mixture
  3. customthe organic layer was separated
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-ebc8795a9ed044dfbb706bb91aad0322
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Reaction notes

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