8-Hydroxyquinoline → 8-Hydrazinylquinoline

Participants

Reaction Conditions

Reaction Steps

A solution of hydrazine in water (equivalent to 250 ml of 100% hydrazine hydrate) was added to the 8-hydroxyquinoline and the mixture was refluxed under nitrogen for 68 hours. After cooling to about 40° C., brine was added and the mixture was extracted with benzene. The benzene solution was washed once with brine, three times with Claisen's alkali (prepared by dissolving 35 g of potassium hydroxide in 25 ml of water, cooling, and adding 100 ml of methanol), twice again with brine, dried over magnesium sulfate, filtered and evaporated to give 60.0 g of an orange oil which crystallized on standing. IR and NMR analysis confirmed the product to be 8-hydrazinoquinoline.

Provenance & Evidence