Synthesis of New 4-Aminoantipyrine derivatives

Abstract

Refluxing of 4-aminoantipyrine with propargyl chloride or p-chloro propinyl chloride in the presence of triethylainine gave the 4-(arnino-2-propinyl) antipyrine (2) or 4-[(aminopropinyl)-3-chloro)] antipyrine (3) respectively in good yield. When compound (2) was refluxed with secondary amines and paraformaldehyde in the presence of cuprous chloride, the corresponding Mannich Bases (4-10) were achieved, while the reaction of compound (3) with secondary amines in boiling ethanol gave the 4-(amino propinyl-3-alkyl/ary! amino) antipyrine (11-16) in quantitative yields. The intended compounds were identified by their IR, UV spectra and CRN. analyses data.