5-Fluoroquinolin-8-amine → 5-Fluoro-1,2,3,4-tetrahydroquinolin-8-amine

Beteiligte Stoffe

Reaktionsschritte

To a solution of 5-fluoro-8-nitro-1,2-dihydroquinoline (83.6 mg, 0.43 mmol) in EtOAc (10 mL) was added a slurry of 10% Pd/C (28 mg) in IMS (3 mL) and the reaction mixture was stirred at RT under a hydrogen atmosphere for 22 h. The suspension was then filtered through a pad of Celite® and the filtrate was concentrated in vacuo affording a mixture of the title compound and 5-fluoroquinolin-8-ylamine as a purple oil (70.4 mg, 99%). 1H NMR (CDCl3, 300 MHz) (signals due to title compound): 6.46 (1H, dd, J=8.5, 5.5 Hz), 6.28 (1H, dd, J=9.2, 8.5 Hz), 3.31-3.28 (2H, m), 3.24 (3H, bs), 2.72 (2H, t, J=6.5 Hz), 1.94-1.86 (2H, m)

Herkunft & Nachweise