Reaction of substituted benzenes and chloral. VII. Reaction of ο-acetotoluidide and chloral was written by Yasue, Masaichi;Takai, Yoshiharu;Yoshizawa, Shigeru. And the article was included in Yakugaku Zasshi in 1957.HPLC of Formula: 60710-80-7 This article mentions the following:
O-Acetotoluidide (30 g.), 33 g. CCl3CH(OH)2, and 100 ml. concentrated H2SO4 heated 20 hrs. at 50-60°, the product poured over ice, let stand overnight, the precipitate filtered off, washed with H2O, refluxed with 700 ml. H2O, cooled, the precipitate filtered off, and extracted with C6H6 gave 12 g. C6H6-soluble portion (I) and a small amount of C6H6-insoluble portion (II); the above reaction 3 weeks at 10-15° yielded 6.7 g. I and 13.5 g. II (this yielded 0.5 g. substance, m. 158-65°); the reaction 10 days at 20° yielded 13 g. I and 3.5 g. II. I (12 g.) in 80 ml. AcOH treated portionwise with 15 g. Zn, heated 4 hrs. on an H2O bath, the solution filtered while hot, the filtrate neutralized with NH4OH, the solution concentrated in vacuo, and the residue extracted with C6H6 gave 2.1 g. 2,5-Me(Cl2CHCH2)C6H3NHAc (III), needles, m. 155.5-6° (EtOH). III (1.7 g.) in 30 ml. EtOH and 0.5 g. NaOH in 10 ml. EtOH refluxed 1 hr., the EtOH removed by heating with 1 g. NH4Cl and 2 ml. H2O, and the residue extracted with C6H6 gave 1.2 g. 2,5-Me(ClCH:CH)C6H3NHAc (IV), needles, m. 173-3.5° (EtOH). IV (0.9 g.) in 50 ml. Me2CO treated dropwise with 1.5 g. KMnO4 in 40 ml. H2O, let stand 2 hrs., the solution decolorized with Na2SO3 and concentrated, the residue acidified with 10% H2SO4, and the product recrystallized from EtOH gave 4,3-Me(AcNH)C6H3CO2H (V), needles, m. 277°. II (13 g.), 80 ml. AcOH, and 15 g. Zn was heated 4 hrs.; the product in a small amount of EtOH gave 0.1 g. insoluble [4,3-Me(AcNH)C6H3]2C2H4, needles, m. 298°, and the filtrate gave III, m. 156°. 4,3-Me(O2N)C6H3CN (10 g.), 25 g. Sn, and 100 ml. EtOH at 25-45° treated with 70 ml. concentrated H2SO4, heated until a clear solution was obtained, the EtOH removed, the residue made alk. with NaOH, and extracted with Et2O gave 8 g. 4,3-Me(H2N)C6H3CN (VI), m. 76-8°. VI (8 g.) and 15 ml. Ac2O refluxed 1 hr. and the product diluted with 100 ml. H2O gave 10 g. 4,3-Me(AcNH)C6H3CN (VII), m. 153-4° (EtOH). VII (8 g.), 150 ml. EtOH, 50 ml. 30% H2O2, and 4 ml. 10% NaOH let stand overnight, the EtOH removed, and the residue recrystallized from H2O gave 6 g. 4,3-Me(AcNH)C6H3CONH2 (VIII), columns, m. 185-7°. VIII (4 g.) and 50 ml. concentrated H2SO4 at 0° treated portionwise with 2.5 g. NaNO2, let stand 1 hr. at room temperature, the precipitate filtered off, taken up in 10% Na2CO3, the solution filtered, the filtrate acidified with 10% H2SO4, and the product recrystallized from 50% EtOH gave 2.5 g. V, needles, m. 278°. V (0.5 g.), 5 ml. AcOH, 5 ml. concentrated HCl, and 2.5 ml. H2O heated 30 min. on an H2O bath, the product made alk. with NH4OH, evaporated to dryness, and the residue recrystallized from H2O gave 4,3-Me(H2N)C6H3CO2H, columns, m. 164°. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7HPLC of Formula: 60710-80-7).
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. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.HPLC of Formula: 60710-80-7
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts