Tetrahydrofuran → 2-(8-Fluoro-6-nitro-3,4-dihydroquinolin-1(2H)-yl)-N,N-dimethylethanamine

Temperature

0 °C

1-(2-(Dimethylamino)ethyl)-8-fluoro-6-nitro-3,4-dihydroquinolin-2(1H)-one (600 mg, 2.13 mmol) was added to a round bottom flask equipped with a stir bar. The flask was sealed and purged with argon. Borane.THF (1M solution in THF, 21.3 mL, 21.3 mmol) was added to the starting material and stirred to dissolve. The reaction mixture was heated to reflux overnight. The reaction was cooled to 0° C. and then quenched with methanol (20 mL). The mixture was then concentrated in vacuo, redissolved in methanol and refluxed for 4 h. The mixture was then concentrated onto silica gel and chromatographed using 0-10% (2M NH3 in MeOH) in dichloromethane. Yield: 364 mg, 64%. 1H NMR (CDCl3) δ 1.95 (m, 2H), 2.27 (s, 6H), 2.56 (m, 2H), 2.77 (m, 2H), 3.41 (m, 4H), 7.69 (m, 1H), 7.77 (dd, 1H, J=9 Hz, 2.7 Hz). EI-MS: 58 (100).

1. customequipped with a stir bar
2. customThe flask was sealed
3. custompurged with argon
4. dissolutionto dissolve
5. temperatureThe reaction mixture was heated
6. temperatureto reflux overnight
7. customquenched with methanol (20 mL)
8. concentrationThe mixture was then concentrated in vacuo
9. dissolutionredissolved in methanol
10. temperaturerefluxed for 4 h
11. concentrationThe mixture was then concentrated onto silica gel
12. customchromatographed

ORD record

ord-14625a0434cf418993df53e9c69f841e

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173813B2