反应详情

Triethylamine (31.88 mL, 228.77 mmol, 1.5 eq) was added to a solution of 7-benzyloxy-4-chloro-3-nitroquinoline (48.00 g, 152.51 mmol, 1 eq) in dichloromethane (400 mL). Dropwise addition of 2,2-dimethyl-1,3-dioxolan-4-methanamine (20.0 g, 152.51 mmol, 1 eq) to the reaction mixture followed, which was then stirred at ambient temperature for 6 hours. The crude reaction mixture was concentrated under reduced pressure, and the resulting solid was triturated with water and then stirred for 1 hour. The precipitate was collected by filtration, washed with water, dried, suspended in diethyl ether (400 mL), sonicated, and the resulting precipitate material was collected by filtration. The product was dried under vacuum at 40° C. for 12 hours to afford 60.1 g of (7-benzyloxy-3-nitro-quinolin-4-yl)[(2,2-dimethyl[1,3]dioxolan-4-yl)methyl]amine as a yellow solid, mp 154-155° C. 1H-NMR (300 MHz, CDCl3) δ 9.74-9.62 (br m, 1H), 9.32 (s, 1H), 8.15 (d, J=9.4 Hz, 1H), 7.51-7.31 (m, 6H), 7.15 (dd, J=9.4, 2.7 Hz, 1H), 5.21 (s, 2H), 4.48-4.37 (m, 1H), 4.16-4.05 (m, 2H), 4.04-3.93 (m, 1H), 3.74 (dd, J=8.5, 5.9 Hz, 1H), 1.54 (s, 3H), 1.40 (s, 3H); MS (APCI) m/z 410.1 (M+H)+.

1. customThe crude reaction mixture
2. concentrationwas concentrated under reduced pressure
3. customthe resulting solid was triturated with water
4. stirringstirred for 1 hour
5. filtrationThe precipitate was collected by filtration
6. washwashed with water
7. customdried
8. customsonicated
9. filtrationthe resulting precipitate material was collected by filtration
10. customThe product was dried under vacuum at 40° C. for 12 hours