3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-amine (6) was synthesized as follows: 1,1,4,4,6-pentamethyl-7-nitro-1,2,3,4-tetrahydronaphthalene (5) (2.5 g, 10.1 mmol) was dissolved in ethyl acetate (205 mL) to prepare a 0.05 M solution. The hydrogenation reaction was repeated twice using a ThalesNano H-cube?reactor at 70°C and 2-5 bar pressure through a 10 mL Pd/C cartridge at a flow rate of 1.0 mL/min. Upon completion of the reaction, the resulting solution was concentrated under vacuum to afford the target product 6 (2.13 g, 97% yield) as a yellow crystalline solid with a melting point of 205°C. The structure of the product was confirmed by the following characterization data: 1H NMR (400 MHz, CDCl3) δ 7.00 (s, 1H), 6.63 (s, 1H), 3.34 (br s, 2H), 2.15 (s, 3H), 1.63 (s, 4H), 1.26 (s, 12H); 13C NMR (100.6 MHz, CDCl3) δ 143.5, 142.0, 135.2, 128.3, 120.5, 112.6, 35.3, 35.2, 33.8, 33.4, 32.0, 31.8, 17.1; IR ( neat)ν 3404, 3335, 2956, 2925, 1626, 1504 cm-1; LC-MS-CI (M+H)+ calculated value C15H24N 218.1909, measured value 218.1908.
