Uses
4-Methylnaphthalen-1-amine can be used in organic synthesis, particularly for developing specialized dyes, pigments, and functional materials.
Synthesis
General procedure for the synthesis of 4-methylnaphthalen-1-amine from 1-methyl-4-nitronaphthalene: To a solution of 1-methyl-4-nitronaphthalene (4.0 g, 21 mmol) in ethanol (300 mL) was added Raney-Ni (about 4 scoops). The reaction mixture was stirred under hydrogen (1 atm) atmosphere for 16 hours. Upon completion of the reaction, the catalyst was removed by filtration through a diatomaceous earth pad and the filtrate was concentrated. Finally, the target product 4-methylnaphthalen-1-amine (3.2 g, 75% yield) was purified by silica gel fast column chromatography (eluent ratio ethyl acetate:hexane = 15:85).
References
[1] Chinese Journal of Chemistry, 2017, vol. 35, # 10, p. 1595 - 1600
[2] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 3, p. 719 - 728
[3] Patent: WO2006/26356, 2006, A2. Location in patent: Page/Page column 42
[4] Justus Liebigs Annalen der Chemie, 1913, vol. 402, p. 28
[5] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1955, vol. 28, p. 115,117; engl. Ausg. S. 109
