Hydrochloric Acid → 5-Chloropyrazinoic acid

HRID 1520241Notes

Reaction equation

HRID 1520241 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.O.[OH-].[Li+].Cl>C1COCC1.O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 406081Methyl 5-chloropyrazine-2-carboxylate

Product 1

HCID 4654725-Chloropyrazinoic acidYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-chloropyrazine-2-carboxylate (CAS [33332-25-1], 1 g, 5.79 mmol) was dissolved in a mixture of THF (50 ml) and water (50 ml). Lithium hydroxide monohydrate (243 mg, 5.79 mmol) was added and the reaction mixture was stirred at RT overnight. The pH was adjusted to 1 with 1M HCl and the product was extracted with three portions of EtOAc. The combined organic layers were dried over Na2SO4 and concentrated under vacuum. The crude material was purified by flash chromatography (SiO2, 50 g, 0 to 20% MeOH in DCM) to yield the title compound as white solid (741 mg, 81%). MS (ISP): m/z=159.0 [M+H]+.

Workup

  1. extractionthe product was extracted with three portions of EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customThe crude material was purified by flash chromatography (SiO2, 50 g, 0 to 20% MeOH in DCM)

Sources & evidence

ORD record
ord-46e0e36f917946f7891f572be78bbe72
Source dataset
uspto-grants-2015_07
Patent number
US09073909B2

Reaction notes

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