Water → Methyl 3-aminopyrazinecarboxylate

HRID 864312Notes

Reaction equation

HRID 864312 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.S(=O)(=O)(O)O.O.[C:17](=O)(O)[O-].[Na+]>CO>[NH2:1][C:2]1[C:3]([C:8]([O:10][CH3:17])=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 726563-Amino-2-pyrazinecarboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 72669Methyl 3-aminopyrazinecarboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Aminopyrazine-2-carboxylic acid (55.5 g, 0.4 mol) is suspended in 400 mL of methanol, cooled in an ice bath and concentrated sulfuric acid (80 mL) is gradually added with stirring and stirring then continued for 48 hours at room temperature. The resulting dark brown solution is poured into 700 mL of water containing sodium bicarbonate (160 g). The brown crystalline solid which precipitates is collected and dried. The crude product is purified by recrystallization from water to yield the product as yellow needles in 63% yield, melting point 169°-170° C.

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirring
  3. customThe brown crystalline solid which precipitates
  4. customis collected
  5. customdried
  6. customThe crude product is purified by recrystallization from water

Sources & evidence

ORD record
ord-5eb8f60fa02f4d528e9c9925fdc64bae
Source dataset
uspto-grants-1996_10
Patent number
US05563113

Reaction notes

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