Hydrochloric Acid → HCID 12841582, compound

HRID 646663Notes

Reaction equation

HRID 646663 reaction equation
[NH2:1][C:2]1[C:3]([C:14]([O:16]C)=[O:15])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:7]=1.[OH-].[Na+].Cl>CO>[NH2:1][C:2]1[C:3]([C:14]([OH:16])=[O:15])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12841581HCID 12841581, compound

Product 1

HCID 12841582HCID 12841582, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-amino-6-phenylpyrazine-2-carboxylate (1.2 g, 5.26 mmol) in methanol (5 mL) was added 6.0 N aqueous sodium hydroxide (6 mL) at room temperature. The solution was stirred at 50 C. for 3 h. The reaction was neutralized slowly by adding 2.0 N hydrochloric acid until the pH of the solution became in the 2-3 range at 0° C. The solution was extracted with ethyl acetate (50 mL). The organic layer was washed with saturated aqueous sodium chloride (50 mL) and dried over magnesium sulfate. Filtration and concentration at reduced pressure afforded 3-amino-6-phenylpyrazine-2-carboxylic acid (0.59 g, 52% yield): MS (EI) for C11H9O2: 216 (MH+)

Workup

  1. custombecame in the 2-3 range at 0° C
  2. extractionThe solution was extracted with ethyl acetate (50 mL)
  3. washThe organic layer was washed with saturated aqueous sodium chloride (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and concentration at reduced pressure

Sources & evidence

ORD record
ord-d5ffaea025184d95a16032ee55b06438
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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