Hydrogen Peroxide → 6-Fluoroquinoxaline-2-carboxylic acid

HRID 1826918Notes

Reaction equation

HRID 1826918 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]=[O:13])[CH:6]=[N:5]2.[OH:14]O>C(O)=O.Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[N:5]2

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 221364416-Fluoroquinoxaline-2-carbaldehyde

Product 1

HCID 221364266-Fluoroquinoxaline-2-carboxylic acidYield 45%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

Using the method of Dodd (Synthesis, 1993, 295–297), a solution of 6-fluoroquinoxaline-2-carboxaldehyde (71 mg, 0.4 mmol) in formic acid (2 mL) was cooled in an ice bath and treated with hydrogen peroxide (2 mL of 30%). The reaction was stirred in the ice bath for 3 hours. After this time the reaction mixture was diluted with 10% HCl (25 mL) and extracted with dichloromethane (4×25 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered and concentrated to afford 35 mg (45%) of 6-fluoroquinoxaline-2-carboxylic acid.

Workup

  1. customthe method of Dodd (Synthesis, 1993, 295–297)
  2. extractionextracted with dichloromethane (4×25 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-86d4cae0c6ae4001baedc53d507ef9d9
Source dataset
uspto-grants-2006_05
Patent number
US07053104B2

Reaction notes

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