Benzaldehyde → 5-Benzoylpyrazine-2-carboxylic acid

HRID 1821785Notes

Reaction equation

HRID 1821785 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=[O:8].[CH:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.S(=O)(=O)(O)O.C(OOC(C)(C)C)(C)(C)C>O.C(O)(=O)C>[C:10]([C:5]1[N:4]=[CH:3][C:2]([C:7]([OH:9])=[O:8])=[N:1][CH:6]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 10472-Pyrazinecarboxylic acidHCID 1118Sulfuric AcidHCID 8033Di-tert-butyl peroxide

Product 1

HCID 4780045-Benzoylpyrazine-2-carboxylic acidYield 36%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred, cooled (0° C.) solution of 2-pyrazine carboxylic acid (3.0 g, 24.2 mmol) and benzaldehyde (7.4 mL; 73 mmol) in a 50% aqueous solution of sulfuric acid (40 mL) and 25 mL of acetic acid was added FeSO4 7 H2O (20.3 g, 73 mmol dissolved in 50 mL of water) and t-butyl peroxide (9.2 mL; 73 mmol) simultaneously. After stirring for 1 hour, the reaction was treated with 200 mL of water. A precipitate formed which was filtered and washed with methylene chloride (3×100 mL) to yield a tan solid (36% yield).

Workup

  1. customA precipitate formed which
  2. filtrationwas filtered
  3. washwashed with methylene chloride (3×100 mL)

Sources & evidence

ORD record
ord-362d1060611f44468d2bb6c39266c8bb
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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