Hydrazine hydrate (1:1) → 6-Chloro-3-hydrazinyl-4-methylpyridazine

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The hydrazino pyridazine starting materials can be prepared by known procedures. For example, 3,6-dichloro-4-methylpyridazine heated at reflux with excess hydrazine hydrate (50 percent in water) for 0.3 to 1 hour produces 3-chloro-4-methyl-6-hydrazinopyridazine and 3-chloro-5-methyl-6-hydrazinopyridazine. The isomers can be separated by fractional crystallization using ethanol as a solvent. See, Takahayashi, Pharm. Bull., 5, 229 (1957); Chem. Abstr. 52:6359, Linholter et al., Acta Chem. Scand. 16, 2389 (1962); Chem. Abstr. 59:1632g, Steck et al., J. Amer. Chem. Soc., 76, 4454 (1954) and Horning et al., J. Org. Chem., 20, 707 (1955).

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