5-Nitroanthranilonitrile

yellow to brownish powder. 2-Amino-5-nitrobenzonitrile [17420-30-3], 2-cyano-4-nitroaniline, Mr 163.13, mp 210℃, is readily soluble in acetone, chloroform, and benzene; it is sparingly soluble in water and ethanol. As already mentioned, the reaction of 2-chloro5-nitrobenzonitrile with ammonia gives 2-amino-5-nitrobenzonitrile, an intermediate for azo dyes.

A newer synthetic route starts from 6-nitroisatoic anhydride [2H-3,1-benzoxazine-6-nitro-2,4 (1H)-dione]: the latter is converted into 2-amino-5-nitrobenzonitrile by reaction with ammonia, subsequent treatment with phosgene in dimethylformamide or Nmethylpyrrolidone, followed by hydrolysis of the formamidine.

Journal of the American Chemical Society, 82, p. 3152, 1960 DOI: 10.1021/ja01497a043