4-Aminoantipyrine → 2,3-Dimethyl-4-hydroxyamino-1-phenyl-3-pyrazolin-5-one

HRID 962919

Reaction equation

HRID 962919 reaction equation
[CH3:1][C:2]1[N:7]([CH3:8])[N:6]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:4](=[O:5])[C:3]=1[NH2:15].I(C1C=CC=CC=1)=[O:17]>P([O-])([O-])([O-])=O>[CH3:8][N:7]1[C:2]([CH3:1])=[C:3]([NH:15][OH:17])[C:4](=[O:5])[N:6]1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 21514-AminoantipyrineHCID 92125Iodosylbenzene

Product 1

HCID 189134602,3-Dimethyl-4-hydroxyamino-1-phenyl-3-pyrazolin-5-oneYield 30%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Conditions

Temperature
0 °C

Procedure

4-Aminoantipyrine (0.12 mmol, Aldrich) and octachloro-octachloro tetrasulfonato Fe(III) porphyrin (0.6 μmol) were dissolved in 4 ml of pH 7 phosphate buffer and cooled to 0° C. To this was added iodosobenzene (66 mg, 0.3 mmol) was added in portions over 10 min. The reaction was stirred for 4 hr and extracted with 3×2 ml of methylene chloride and dried over Na2CO3. The organic layer was chromatographed over silica gel, eluting with methylene chloride, to yield 2,3-dimethyl-4-hydroxyamino-1-phenyl-3-pyrazolin-5-one (AP-3) in 30% yield.

Workup

  1. additionwas added in portions over 10 min
  2. extractionextracted with 3×2 ml of methylene chloride
  3. dry with materialdried over Na2CO3
  4. customThe organic layer was chromatographed over silica gel
  5. washeluting with methylene chloride

Sources & evidence

ORD record
ord-bc43956ba2d54672a36cc35126f77b66
Source dataset
uspto-grants-1998_06
Patent number
US05760216

Linked notes

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