Some derivatives of 4′-hydroxydiphenylamine-4-carboxylic acid was written by Burger, Alfred;Darby, Robert A.. And the article was included in Journal of the American Chemical Society in 1955.Category: nitriles-buliding-blocks The following contents are mentioned in the article:
p-HOC6H4NHPh (260 g.), 375 g. Bz2O, and 250 cc. dry pyridine heated 6 h. on the steam bath, the cooled mixture acidified with cold 50% H2SO4 and filtered, the brownish residue washed with 2% aqueous NaOH and H2O, treated with EtOH and diluted with H2O, and the precipitate crystallized from aqueous EtOH gave 330 g. p-BzOC6H4NHPh, pale yellow leaflets, m. 112-14°. p-BzOC6H4NHC6H4Br-p (40 g.) and 16 g. CuCN in 240 cc. dry quinoline refluxed 6 h., the red solution cooled and poured with stirring into 200 cc. 37% HCl, and the precipitate filtered, washed, and recrystallized from C6H6-ligroine gave 17.5 g. p-BzOC6H4NHC6H4CN-p (I), almost colorless needles, m. 178.5-80.5° (all m.ps. are corrected). I treated 0.5 h. with hot KOH in EtOH gave 71% p-HOC6H4NHC6H4CN-p (II), m. 193-4.5° (from aqueous EtOH). II treated with CH2N2 gave the Me ether (III), m. 99-100° (from aqueous Me2CO). III refluxed 20 h. with 15% alc. KOH yielded 43% p-MeOC6H4NHC6H4CO2H-p (IV), m. 165-7° (from MeOH). II (5 g.) in 40 cc. (CH2OH)2 containing 6 g. KOH refluxed 3 h., cooled, acidified, and filtered, and the brown crystalline filter residue recrystallized with Darco from MeOH yielded 3.56 g. p-HOC6H4NHC6H4CO2H-p, colorless crystals, m. 229-30° (decomposition) (it turned pink in air), which treated with CH2N2 gave the Me ester of IV, m. 91.5-3.5° (from Et2O-ligroine). II (0.1 mol) treated with 0.4 mol ICl and the resulting pink powder (which turned blue in air) recrystallized repeatedly from Et2O-ligroine gave 30% 3,5,4-Cl2(HO)C6H2NHC6H4CN-p, almost transparent colorless needles, m. 215-16° (from Et2O-ligroine). This study involved multiple reactions and reactants, such as 4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1Category: nitriles-buliding-blocks).
4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Category: nitriles-buliding-blocks
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts