Hydrazine hydrate (1:1) → 2-Hydrazinyl-6-methylpyridine

A mixture of 2-chloro-6-methylpyridine (50.6 g, 397 mmol) and hydrazine hydrate (80 mL, 1.65 mol) was heated under reflux for 20 hours. The reaction solution was allowed to cool to room temperature, and excess hydrazine hydrate was evaporated under reduced pressure, and the residue was poured into water. The solution was made basic by the addition of a sodium hydroxide solution, and the organic matter was extracted with chloroform. The extract was washed with saturated brine and water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was chilled to crystallize, and the resulting crystals were washed with petroleum ether to give the title compound (31.0 g, 63% yield).

1. temperaturewas heated