Hydrochloric Acid → (E)-4-[4-(1H-Imidazol-1-yl)phenoxy]-2-buten-1-amine

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Reaction Steps

A solution of 26.2 g of (E)2-[4-[4-(1H-imidazol-1-yl)phenoxy]-2-buten-1-yl]-1H-isoindole-1,3(2H)-dione (Example 30) in 1 liter of ethanol is treated with 5 ml of anhydrous hydrazine, and the mixture stirred at reflux for 18 hours. To the reaction mixture is added 25 ml of concentrated HCl and the mixture cooled to room temperature. The precipitate is collected and washed with 2 portions of 300 ml of water. The filtrate and aqueous washes are combined and taken to dryness in vacuo. The solid is treated with 25 ml of 10N NaOH, the mixture saturated with solid K2CO3, and then extracted with 500 ml of dichloro-methane. Removal of the dichloromethane in vacuo leaves a viscous oil that solidifies at room temperature. A portion is purified by recrystallization from hexane, and dried; m.p. 81°-83° C.; yield, 0.5 g.

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