Hydrochloric Acid → HCID 23364083, compound

HRID 1081324Notes

Reaction equation

HRID 1081324 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1.[N:12]1[CH:17]=[CH:16][N:15]=[C:14]2[C:18]([O:20][C:21](=[O:22])[C:13]=12)=[O:19].Cl>C1COCC1>[F:11][C:8]1[CH:9]=[CH:10][C:5]([C:18]([C:14]2[C:13]([C:21]([OH:22])=[O:20])=[N:12][CH:17]=[CH:16][N:15]=2)=[O:19])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 99931-Bromo-4-fluorobenzeneHCID 78482Furo(3,4-b)pyrazine-5,7-dioneHCID 5462224Magnesium

Product 1

HCID 23364083HCID 23364083, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of magnesium (4.2 g) in THF (20 ml) was added iodine (catalytic amount) while stirring at room temperature under argon atmosphere. To the mixture was then added dropwise a solution of 1-bromo-4-fluorobenzene (22.8 g) in THF (60 ml), and the mixture was stirred for 30 minutes. The mixture was added dropwise, while stirring at room temperature, to a solution of 2,3-pyrazinedicarboxylic anhydride (20.0 g) in THF (100 ml), followed by stirring for one hour. The reaction mixture was poured into dilute HCl (adjusting the pH to 4 to 5), followed by extraction with ethyl acetate. The extract solution was washed with water and dried, then the solvent was distilled off to give 3-(4-fluorobenzoyl)-2-pyrazinecarboxylic acid as a colorless oily product (25.8 g).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. additionThe mixture was added dropwise
  3. stirringby stirring for one hour
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe extract solution was washed with water
  6. customdried
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-ec33837871954d51b4f8a50cee3760b9
Source dataset
uspto-grants-1996_12
Patent number
US05585385

Reaction notes

Loading…