Ammonia → 2-Anthracen-9-yl-ethylamine

Participants

Reaction Steps

To a solution of anthracen-9-yl-acetonitrile (3.0 g, 13.82 mmol) in ethanol (150 mL) was added concentrated NH4OH (15 mL) and Raney nickel (15 g), and ammonia gas was bubbled through the mixture at 0° C. for 10 minutes. The suspension was hydrogenated for 48 hours at room temperature. Air was bubbled through the solution and Raney nickel was removed by filtration. The filtrate was concentrated and the oily residue was dissolved in CH2Cl2, washed with an aqueous solution of sodium carbonate (Na2CO3, 10%), dried over MgSO4 and concentrated. The resulting solid was purified by recrystallization from a mixture of hexane and CH2Cl2 (7:3) to give 2-anthracen-9-yl-ethylamine as yellow crystals (2.60 g, 85%). 1H NMR (CDCl3) δ 8.37 (1H, s), 8.33 (2H, d), 8.02 (2H, d), 7.54-7.47 (4H, m), 3.86 (2H, t), 3.19 (2H, t), 1.34 (2H, br-s).

Provenance & Evidence