Neuere Methoden der präparativen organischen Chemie II. 7. Alkylierung aromatischer Amine

The Isolation of N-tert-Butyl-p-Toluidine Hydrochloride and the Synthesis of Mauveine

“…15 This type of reaction has also been used to make 2,6-diisopropyl-p-toluidine by reacting p-toluidine with propene or propanol and a Lewis acid. 16 The ready availability of N-tert-butyl-p-toluidine hydrochloride has allowed us to perform more experiments to study the synthesis of mauveine. By carrying out many experiments, each using 373 mg of N-tert-butyl-p-toluidine hydrochloride, we found that the oxidation of N-tert-butyl-ptoluidine hydrochloride : o-toluidine : aniline (1.0 : 1.5 : 3.0) with K 2 Cr 2 O 7 in dilute sulfuric acid at 40-45 °C for 12 h gave a good ratio of mauveine A to mauveine B which approximated to authentic mauveine (Scheme 3).…”

Base-Catalyzed Hydroamination of Olefins: An Environmentally Friendly Route to Amines

“…[2a] Similarly, aniline is converted to N-ethylaniline using Na or NaNH 2 as precatalyst at 250 ± 300 8C and 50 ± 200 bar pressure. [16,22] The reaction temperature and pressure for the amination of ethylene can be considerably lowered by using alkali metal amides [15,16,23] and supported alkali metals as catalysts. [24] Since they operate at low temperatures these catalysts are particularly useful for the selective formation of monoalkylated amines.…”

Structure-activity Relationships of <i>N</i>-Aryl-4-carboxy- and <i>N</i>-Aryl-4-hydroxy-phthalimides in Control of <i>Plasmodiophora</i> Disease

“…Among N-aryl-4-carboxyphthalimides (A series), only 2, 6-dialkyl series (25-29 and 31) showed preventive activity. Both unsubstituted (1) and monosubstituted derivatives (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13) were inactive. The activity of disubstituted derivatives varied with the physicochemical properties and positions of substituents on the N-aryl ring.…”