Chemical Properties
yellow to brown crystalline powder and chunks
Uses
4-Nitrophenethylamine hydrochloride was used in the synthesis of ortho-metalated primary phenethylamines complexes containing six-membered palladacycles and N-(4-nitrophenethyl)formamide.
Preparation
The preparation of 4-Nitrophenethylamine hydrochloride is as follows:Ten mL of 2M HCl was then added in a one-pot fashion, and, in all cases but threonine, the reaction vessel was heated to 190°Cover 5 min with stirring and then allowed to cool. In the case of the temperature-sensitive threonine, soxhlet extraction with toluene was performed at 80°C to remove R-carvone from the reaction mixture. The aqueous reaction mixture was washed three times with 25 mL of ether, and then water solvent was distilled off from the hydrochloride salt. The hydrochloride salt was transferred to a vacuum oven and dried overnight at 150 °C and 10 Torr.
Synthesis
In a reactor, 140 kg of N-(4-nitrophenylethyl)acetamide was dissolved in 190 kg of ethanol with constant stirring until complete dissolution. The pH of the reaction mixture was adjusted to 1 using 2 mol/L hydrochloric acid solution.Subsequently, the reaction mixture was heated to 80°C and maintained at this temperature for 20 hrs. Upon completion of the reaction, the reaction solution was cooled to room temperature to induce precipitation of the solid product. The crude product was purified by recrystallization through methanol, and after filtration and centrifugation, 116 kg of 4-nitrophenylethylamine hydrochloride was obtained, and the purity of the final product was 99.6%. The yield of this synthesis step was 84.7%.
References
[1] Patent: CN107759477, 2018, A. Location in patent: Paragraph 0063
