Potassium Carbonate → 5-Chloropyrazinoic acid

HRID 388384

Reaction equation

HRID 388384 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10]C)=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 406081Methyl 5-chloropyrazine-2-carboxylate

Product 1

HCID 4654725-Chloropyrazinoic acidYield 72.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 5-chloro-2-pyrazinecarboxylate (Bio-Farma; 1.50 g, 8.69 mmol) in a mixture of methanol (16 ml) and water (8 ml) was stirred at room temperature and treated with potassium carbonate (1.201 g, 8.69 mmol). The resulting solution was stirred for 2 hrs and the methanol removed under reduced pressure. The residue was partitioned between ethyl acetate and water (20 ml) and the aqueous layer acidified by addition of 5M hydrochloric acid. Extraction (×2) with ethyl acetate and drying over MgSO4 followed by removal of the solvent under reduced pressure, gave the title compound (1.00 g) as a white solid;

Workup

  1. stirringThe resulting solution was stirred for 2 hrs
  2. customthe methanol removed under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and water (20 ml)
  4. additionthe aqueous layer acidified by addition of 5M hydrochloric acid
  5. extractionExtraction (×2) with ethyl acetate
  6. dry with materialdrying over MgSO4
  7. customfollowed by removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-ba30737b57bc4b459ce1bb5842ea681e
Source dataset
uspto-grants-2013_02
Patent number
US08377941B2

Linked notes

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