Hydrogen Peroxide → HCID 136463822, compound

HRID 862097Notes

Reaction equation

HRID 862097 reaction equation
[C:1]([O:5]/[N:6]=[C:7](\[C:17]1[C:22]([OH:23])=[CH:21][CH:20]=[CH:19][N:18]=1)/[C:8]1[CH:13]=[C:12]([C:14]#[N:15])[CH:11]=[CH:10][C:9]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].OO.S([O-])(O)(=O)=[O:29].[K+]>C(O)C>[C:1]([O:5]/[N:6]=[C:7](\[C:17]1[C:22]([OH:23])=[CH:21][CH:20]=[CH:19][N:18]=1)/[C:8]1[CH:13]=[C:12]([C:14](=[O:29])[NH2:15])[CH:11]=[CH:10][C:9]=1[OH:16])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 135496353HCID 135496353, compound

Product 1

HCID 136463822HCID 136463822, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (Z)-2-(5-cyano-2-hydroxybenzoyl)-3-hydroxypyridine O-t-butyloxime (0.98 g) in ethanol (20 ml) were added at 0° C. 6N NaOH (0.15 ml) and 30% aqueous solution of hydrogen peroxide (1.5 ml). The mixture was stirred for 2 hours at temperatures ranging from 50° to 60° C. The reaction mixture was cooled by aeration, which was then neutralized with a saturated aqueous solution of potassium hydrogensulfate, then the solvent was concentrated. The concentrate was subjected to extraction with chloroform and dried (anhydrous magnesium sulfate), followed by distilling off the solvent. The residue was recrystallized from chloroform to give (Z)-2-(5-carbamoyl-2-hydroxybenzoyl)-3-hydroxypyridine O-t-butyloxime (0.42 g) (Compound 71).

Workup

  1. customranging from 50° to 60° C
  2. temperatureThe reaction mixture was cooled by aeration, which
  3. concentrationthe solvent was concentrated
  4. extractionThe concentrate was subjected to extraction with chloroform
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. distillationby distilling off the solvent
  7. customThe residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-e81e6ab661f94be98b8ab86d257f9365
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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