Sodium Chlorite → Antipyric acid

HRID 1851075Notes

Reaction equation

HRID 1851075 reaction equation
[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([CH:14]=[O:15])[C:10](=[O:16])[N:9]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)C1C=CC=CC=1.[O-:23]Cl=O.[Na+]>C(O)CCC>[CH3:1][N:8]1[C:12]([CH3:13])=[C:11]([C:14]([OH:15])=[O:23])[C:10](=[O:16])[N:9]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 23668197Sodium Chlorite2×HCID 86656056HCID 86656056, compound

Product 1

HCID 246564Antipyric acidYield 75.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a mixture of 1-benzyl-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxaldehyde (1 g, 4.624 mmol) in butyl alcohol were added to NaClO2 (1.254 g, 13.873 mmol) in an aqueous solution and potassium phosphate monobasic monohydrate (3.146 g, 23.12 mmol) in an aqueous solution slowly at 0° C. The resulting reaction mixture was slowly heated to room temperature and stirred for 10 hours. NaClO3 (1 g) was further added while monitoring the reaction. Following the addition of sodium chlorite, the reaction mixture was stirred and then extracted with ethyl acetate. The organic layer was washed with, dried with Na2SO4 and then filtered. The filtrate was concentrated under reduced pressure. The resulting residue was washed with 20% ethyl acetate solution in small amount of hexane. The target compound was obtained as a white solid (808 mg, 3.48 mmol, 75% yield).

Workup

  1. customThe resulting reaction mixture
  2. customthe reaction
  3. stirringthe reaction mixture was stirred
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with,
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. washThe resulting residue was washed with 20% ethyl acetate solution in small amount of hexane

Sources & evidence

ORD record
ord-ebaa40dced76474b82127b26ec24f002
Source dataset
uspto-grants-2015_02
Patent number
US08957102B2

Reaction notes

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