Acetic Acid → HCID 59807049, compound

Participants

Reaction Steps

A solution of 6-nitro-1-(2-oxopropyl)-3,4-dihydroquinolin-2(1H)-one (500 mg, 2.01 mmol) and pyrrolidine (333 μL, 4.03 mmol) in 10 mL 1,2-dichloroethane (DCE) was treated with acetic acid (228 μL, 4.03 mmol) followed by sodium triacetoxyborohydride (1.27 g, 6.03 mmol). The suspension was stirred at room temperature overnight then quenched with 10 mL 1N NaOH. The mixture was diluted with 15 mL H2O then extracted with 2×100 mL CH2Cl2. The combined organic fractions were rinsed with 50 mL H2O, dried over MgSO4, filtered and concentrated to give a yellow residue which was subjected to flash chromatography on silica gel using 5% 2M NH3 in MeOH/CH2Cl2. A yellow oil was obtained (595 mg, 97.5%). 1H-NMR (CDCl3) δ: 8.13 (dd, J=2.7, 9.0 Hz, 1H), 8.07 (d, J=2.7 Hz, 1H), 7.21 (d, J=9.0 Hz, 1H), 4.21 (dd, J=8.7, 14.1 Hz, 1H), 4.02 (dd, J=5.4, 14.4 Hz, 1H), 3.00 (t, J=7.2 Hz, 2H), 2.91-2.62 (m, 7H), 1.92-1.90 (m, 4H), 1.00 (d, J=6.3 Hz, 3H).

Provenance & Evidence