Studies on Cinnolines. II. On Nitration of Cinnoline 1-Oxide

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Cinnoline 1-oxide (1) gave 4-nitrocinnoline 1-oxide (II) and a small amount of 5-nitrocinnoline 1-oxide (V) on warming with nitric and sulfuric acids, and gave 4, 5-dinitrocinnoline 1-oxide (IV) by using fuming nitric acid in sulfuric acid. The nitration of I with benzoyl nitrate afforded 3-nitrocinnoline 1-oxid (VI). I was converted into 4-chlorocinnoline (VIII) on the treatment with phosphoryl chloride.

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