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0 °C

1-(3-(Dimethylamino)propyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (4.23 g, 15.25 mmol) was stirred in borane tetrahydrofuran complex, 1M (76 ml, 76 mmol) at 60° C. overnight. The reaction mixture was then cooled to 0° C. and quenched via addition of methanol. The resulting suspension was concentrated and then stirred in refluxing methanol (50 mL). To this solution was added sodium hydroxide (6.10 g, 153 mmol) as a solution in a minimal amount of water. The resulting mixture was refluxed at 90° C. After 1 h, no free product was observed, only product borane complex. The solution was then diluted with water and acidified with conc HCl and refluxed at 90° C. After 1 h, TLC analysis showed free product, and no borane complex. The mixture was then neutralized via addition of NaOH (3N) and extracted with dichloromethane (3×). 1H NMR (DMSO-d6) δ 7.87 (dd, J=9.3, 3 Hz, 1H), 7.77 (d, J=3 Hz, 1H), 6.68 (d, J=9.6 Hz, 1H), 3.43-3.38 (m, 4H), 2.74 (t, J=6 Hz, 2H), 2.23 (t, J=6.5 Hz, 2H), 2.13 (s, 6H), 1.85 (quint, J=6 Hz, 2H), 1.68 (quint, J=7 Hz, 2H). ESI-MS (m/z, %) 264 (MH+, 100).

1. customat 60° C.
2. customovernight
3. customquenched via addition of methanol
4. concentrationThe resulting suspension was concentrated
5. temperaturein refluxing methanol (50 mL)
6. temperatureThe resulting mixture was refluxed at 90° C
7. temperaturerefluxed at 90° C
8. waitAfter 1 h
9. extractionextracted with dichloromethane (3×)