the neutral fraction was tentatively identified by its glpc re-line, 100-62-9; phenyl azide, 622-37-7; N-methyltention time. carbazole, 1484-12-4; o-nitrotoluene, 88-72-2; m-Hydrolysis of N-Methy1eneaniline.-A solution of 4.9 g of N-methyleneaniline in 200 ml of ether was extracted with three nitrotoluene, 99-08-1 ; p-nitrotoluene~ 99-9g-0* 300 ml-portions of 5% HCl. The acid extracts were combined and made alkaline by the addition of NaOH pellets. The basic Acknowledgment.-This study was carried out under solution was extracted with ether and the ether extract dried with the Agricultural over NazSOc. administered by the Athens, Georgia Area, Richard B. identified as aniline by nmr spectroscopy. 111 Beneothieno[3,2-dlpyrimidine and several of its derivatives have been synthesized. Also described is the first reported example of the [l] benzothieno [3,2-dl-v-triasine ring system.

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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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