4-Aminoantipyrine → 2,3-Dimethyl-4-hydroxyamino-1-phenyl-3-pyrazolin-5-one
Reaktionsgleichung
[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]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
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.