1-(2-Chloro-5-methylphenoxy)-3-[1,1-dimethyl-2-(3-chloro-6-pyridazinyloxy)ethylamino)-2-propanol → Hydrazine hydrate (1:1)

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Reaction Steps

A mixture of 5.7 g of 1-(2-chloro-5-methylphenoxy)-3-[1,1-dimethyl-2-(3-chloro-6-pyridazinyloxy)ethylamino]-2-propanol obtained in (a) above, 20 ml of hydrazine hydrate and 20 ml of ethanol was refluxed overnight with stirring. The solvent was removed under reduced pressure. A solution of the residue in 100 ml of benzene was extracted with 30 ml of 10% hydrochloric acid. The aqueous layer was made alkaline with 10% sodium hydroxide and extracted with chloroform, and the organic layer was dried over magnesium sulfate. The solvent was evaporated. To a solution of the residue in 20 ml of ethanol was added 57 ml of 1N hydrochloric acid, and the solvent was evaporated below 40° C. under reduced pressure. A solution of the residue in ethanol was stored at 0° C. overnight. Recrystallization of the product from methanol-ethanol gave 1.21 g of 1-(2-chloro-5-methylphenoxy)-3-[1,1-dimethyl-2-(3-hydrazino-6-pyridazinyloxy)ethylamino]-2-propanol hydrochloride as pale yellow pillar-like crystals having a melting point of 204.6° to 205.7° C.

Provenance & Evidence