Abstract
The benzylation of 3-(γ-dimethylaminopropoxy)-1 H-indazole with benzyl chloride was studied after using alkaline earth metals and their amides as metalating reagents in liquid ammonia. By the use of calcium and barium amides, benzydamine was obtained in good yields.When the benzylation was carried out by use of alkaline earth or alkali metals (not their amides) in liquid ammonia, 3-(γ-dimethylaminopropoxy)-4, 7-dihydro-1H-indazole and 1-benzyl-3-(γ-dimethylaminopropoxy)-4, 7-dihydro-1H-indazole were formed as by-products.Formation of these by-products was inhibited partially by addition of potassium permanganate. The inhibition was found complete, when sodium metal in liquid ammonia was used.
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