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1-(3-Morpholinopropyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (550 mg, 1.722 mmol) was stirred in borane tetrahydrofuran complex, 1M in THF (17.200 mL, 17.20 mmol) overnight at reflux temperature. The reaction mixture was then cooled to 0° C. and quenched via addition of methanol (10 mL). The solution was then concentrated, and the residue was redissolved in a small amount of methanol and stirred at reflux with 2N HCl for 2 h. The mixture was then neutralized and basified with 3N NaOH and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed in ethyl acetate, followed by 5-10% (2M NH3 in methanol) in dichloromethane, giving the desired 4-(3-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)propyl)morpholine (260 mg, 0.851 mmol, 49.4% yield). 1H NMR (DMSO-d6) δ 7.87 (dd, J=9.3, 2.7 Hz, 1H), 7.77 (d, J=2.7 Hz, 1H), 6.72 (d, J=9.3 Hz, 1H), 3.60-3.56 (m, 4H), 3.45-3.39 (m, 4H), 2.74 (t, J=6 Hz, 2H), 2.35-2.26 (m, 6H), 1.88-1.80 (m, 2H), 1.76-1.66 (m, 2H).

1. customquenched via addition of methanol (10 mL)
2. concentrationThe solution was then concentrated
3. dissolutionthe residue was redissolved in a small amount of methanol
4. temperatureat reflux with 2N HCl for 2 h
5. extractionextracted with dichloromethane (3×)
6. customThe combined organics were dried
7. filtrationfiltered
8. concentrationconcentrated
9. customchromatographed in ethyl acetate