反应详情

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).

1. customwas bubbled through the mixture at 0° C. for 10 minutes
2. customAir was bubbled through the solution and Raney nickel
3. customwas removed by filtration
4. concentrationThe filtrate was concentrated
5. dissolutionthe oily residue was dissolved in CH2Cl2
6. washwashed with an aqueous solution of sodium carbonate (Na2CO3, 10%)
7. dry with materialdried over MgSO4
8. concentrationconcentrated
9. customThe resulting solid was purified by recrystallization from a mixture of hexane and CH2Cl2 (7:3)