Some Important Reactions of 4-Aminoantipyrine (4-AAP)‎

الملخص EN

The new heterocyclic compounds 1, 5-Dimethyl-2-phenyl-4-(5-aryl-4, 5-dihydro-1H-pyrazol-3-ylamino)-1, 2-dihydropyrazol-3-ones (iiia-b) and 1, 5-dimethyl-2-phenyl-4-(5-aryl-4, 5-dihydroisoxazol-3-ylamino)-1, 2-dihydropyrazol-3-ones (iva-b) were synthesized in the first route in this work by refluxing ethologic solution of hydrazine hydrate with N-(1, 5-dimethyl-3-oxo-2-phenyl-2, 3-dihydro-1H-pyrazol-4-yl)cinnamamid (iia) or (E)-3-(4-chlorophenyl)-N-(1, 5-dimethyl-3-oxo-2-phenyl-2, 3-dihydro-1H-pyrazol-4-yl) acrylamide (iib) respectively.

These unsaturated amides were prepared by the reaction of Benz aldehyde or 4-chlorobenzaldehyde with N-(1, 5-dimethyl-3-oxo-2-phenyl-2, 3-dihydro-1H-pyrazol-4-yl) acetamide (i) in refluxing methanol.

This ace amide was prepared by reaction of 4-AAP with acetyl chloride or with acetic anhydride.

In the second route 1,7-dimethyl-2-phenyl-hexahydro-6H-pyrazolo[4,3-e][1, 2, 4]triazine-3, 5-dione (vii) was synthesized by refluxing ethologic solution of hydrazine hydrate (in presence of pyridine) with ethyl 1, 5-dimethyl-3-oxo-2-phenyl-2, 3-dihydro-1H-pyrazol-4-ylcarbamate (vi).

This carbonate was synthesized by the reaction of 4-AAP with pyridine or anhydrous sodium carbonate.

Finally, the reaction of 4-AAP with Benz aldehyde or its 4-chloro derivative afforded the corresponding Schiff bases (va-b).

The structure of these compounds was confirmed by IR & UV Spectra, in addition to the CHN elemental analysis.