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Novel ortho-substituted benzonitriles are synthesized by nitro displacement from o-nitrobenzonitriles and 2,6-dinitrobenzonitriles. The displacing nucleophiles include alkoxides, thiol anions, amines, and azide, chloride, and hydroxide ions.In a recent paper1 we reported a facile synthesis of 3aminobenzo[5]thiophene-2-carboxylate esters from o-nitrobenzonitrilesl We now wish to describe the preparation of ortho-substituted benzonitriles, again by a process involving nucleophilic displacement of nitro groups activated by adjacent cyano functions. The nucleophilic lability of activated nitro groups has been well established by Bunnett and coworkers2 and also by Bolto and Miller.® These authors studied the nucleophilic displacement of various functions activated by ortho and para nitro groups. The relative rate of nitro displacement by piperidine was reported to be more than 200 times that of chlorine and nearly equal to that of fluorine.Numerous examples of activated nitro displacements in substituted benzenes are found in the chemical literature, although most cases involve intramolecular displacement.3 4 The synthetic utility of intermolecular displace-

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