Benzaldehyde → 6-chloro-3-phenyl-[1,2,4]triazolo[3,4-a]phthalazine

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Reaction Conditions

Reaction Steps

Concentrated HCl is gradually added to a suspension of 1-hydrazino-4-chloro-phthalazine (0.1 mole) in water (900 ml) until a clear solution is obtained. Then benzaldehyde (0.1 mole) dissolved in the smallest amount of ethanol possible, is dripped into the obtained solution which is heated to 60°/70° C. and stirred for 10 minutes. The reaction mixture is then cooled, and brought to pH 8 by the addition of aqueous sodium bicarbonate. The hydrazone which forms is recovered by filtration and crystallized from isopropanol (m.p. 174°-75° C.). This hydrazone (0.1 mole) is then suspended in acetic acid (900 ml) containing anhydrous sodium acetate (0.3 mole) and to the obtained suspension a solution of bromine (0.105 mole) in acetic acid (60 ml) is added dropwise. After vigorously stirring for 60 minutes, the reaction mixture is poured into ice-water (5 1) and the solid which separates is recovered by filtration, washed first with a diluted aqueous solution of sodium metabisulfite and then with water, and finally crystallized from isopropanol yielding the compound of the title in 74% yield. M.p. 172°-74° C. Using essentially the same procedure outlined in example 1 above, a number of other 3-substituted-6-chloro-1,2,4-triazolo[3,4-a]phthalazines are prepared having the general formula ##STR17## These compounds, as well as the hydrazone intermediates of formula ##STR18## are described in Table I below.

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