Studies in the Field of Pyridazine Compounds. X¹. A Method for the Synthesis of 6-(Substituted Amino)-3-Pyridazinyl-Hydrazines

Abstract

Recently, the 6-(substituted amino)-3-pyridazinyl-hydrazines^2–4 and their hydrazones¹ became important as peripheral antihypertensive agents. These compounds have been synthesized from 3,6-dichloropyridazine (1) by introducing to the molecule firstly the substituted amine and then the hydrazine moiety^2–4. This process has some disadvantages. It is known that one chlorine atom of 1 can be easily replaced by nucleophilic substitution. The subsequent replacement of the other chlorine atom in 1 is, however, rather difficult⁵. For example, 2 silosequent substitution with hydrazine should be uarried out with agreat excess of hydrazine at elevated temperatures and the product formed is liable to decompose in this basic medium. As a consequence, overail yield of this process is low ana in general, the final product nas to be purifiea tnroilgh its benzylidene derivative. Tnerefore, according to our experiments, this process does not seem to be useful for large-scale operations.