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

Participants

Reaction Steps

90 g (0.626 mol) of 6-methoxy-2-chloropyridine and 313.4 g of hydrazine hydrate were refluxed for 18 hours with stirring. The reaction mixture was cooled and the oil of the bottom layer was separated. The top layer was extracted three times with diethyl ether (total volume of 450 ml). The oil and the bottom layer left after extraction with diethyl ether were distilled under reduced pressure to remove the hydrazine hydrate. The residue was dissolved in 150 ml of a 20% aqueous solution of potassium hydroxide and extracted twice with diethyl ether (total volume 300 ml). The ether extract was dried with potassium hydroxide and combined with the ether solution. The mixture was distilled to afford 22.2 g of the desired product having a boiling point of 144° to 150° C./19-20 mmHg (yield 25%). Upon cooling, the product crystallized providing crystals having a melting point of about 30° to 40° C.

Provenance & Evidence