Improved method for the synthesis of 4-methylanthranilic acid was written by Takatori, Kichitaro;Asano, Shingo;Usui, Fumio. And the article was included in Gifu Yakka Daigaku Kiyo in 1958.Electric Literature of C8H8N2 This article mentions the following:
An improved synthetic method of synthesis of 4-methylanthranilic acid, effective for the treatment of Yoshida sarcoma, is studied. p-Toluidine (30 g.), 60 cc. alc., and 90 cc. 10% KOH is refluxed 1 hr. to give 97% 3-nitro-p-toluidine (I), orange columns, m. 113-14° (60% alc. or ligroine). I (50 g.) in 135 cc. 50% H2SO4 is cooled, treated with 25 g. NaNO2 and 70 cc. H2O at -10°, and stirred to give a reddish orange solution containing 3-nitro-p-toluene-diazonium sulfate. This solution is added to warmed (50°) Cu(CN)2 solution gradually, kept 20 min. more, cooled, and the separated mass extracted with C6H6 to give 76% 3-nitro-p-tolunitrile (II), colorless to light yellow needles, m. 96-8° (H2O). II (20 g.) in 20 g. AcOH is reduced with 90 cc. concentrated HCl and 200 g. leafy Pb at 55-60° to 43%, 3-amino-p-tolunitrile (III), plates, m. 92-4.5° (30% alc.). III (10 g.) and 50 cc. 10% KOH solution is boiled 7 hrs., cooled, neutralized with dilute AcOH, and the precipitate recrystallized from alc. to give 67% 4-methylanthranilic acid (IV), columns, m. 177-8°, violet fluorescence in alc. When this reaction is stopped after boiling only 2 hrs., 2-amino-p-toluamide, plates, m. 144-7°, is obtained. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Electric Literature of C8H8N2).
3-Amino-4-methylbenzonitrile (cas: 60710-80-7) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Electric Literature of C8H8N2
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts