Ethanol → 2-(3-Amino-5-ethyl-2-pyrazolin-1-yl)-6-chloropyridine

Participants

Reaction Steps

A 0.26 g. amount of sodium metal is dissolved in 100 ml. of absolute ethanol, then 8.1 g. of 2-chloro-6-hydrazinopyridine (Example 2) is added followed by 6.4 g. of 3-methoxyvaleronitrile. The reaction mixture is refluxed for 16 hours, then is evaporated in vacuo to give a solid. The solid is dissolved in water/dichloromethane. The organic layer is separated, dried over magnesium sulfate, filtered through anhydrous magnesium silicate and concentrated while adding hexane to yield 7.0 g. of pale yellow crystals. A 200 mg. amount of the crude product is recrystallized from dichloromethanehexane to give 171 mg. of the product of the Example, as pale yellow crystals, m.p. 131°-133° C.

Provenance & Evidence