Step 5: Synthesis of quinolin-6-ylmethylamine
To a saturated ammonia methanol solution (1 L) of quinoline-6-carbonitrile (96 g, 0.62 mol) was added Raney-Ni catalyst (10 g) and the reaction mixture was stirred at room temperature. The reaction was carried out for 16 hours at room temperature and 1 atmosphere of hydrogen at 1 atm. After completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford 6-aminomethylquinoline as a brown oil (80 g, 82% yield).
1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 8.83 (dd, J = 4.2, 1.7 Hz, 1H), 8.29 (d, J = 8.3 Hz, 1H), 7.95 (d, J = 8.6 Hz, 1H), 7.85 (s, 1H), 7.75 (dd, J = 8.7, 1.8 Hz, 1H), 7.49 (dd, J = 8.2, 4.2 Hz, 1H), 3.90 (s, 2H).
