Tetrahydrofuran → 6-Nitro-1-(3-(pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinoline

Participants

Reaction Conditions

Reaction Steps

A solution of 6-nitro-1-(3-(pyrrolidin-1-yl)propyl)-3,4-dihydroquinolin-2(1H)-one (500 mg, 1.648 mmol) in borane tetrahydrofuran complex, 1 M in THF (16.500 mL, 16.50 mmol) was stirred overnight at 60° C. The reaction mixture was then cooled to 0° C., and quenched with methanol. The resulting solution was concentrated, and the residue was stirred in refluxing methanol and 1N HCl for 1 h. The mixture was then neutralized with 1N sodium hydroxide, then extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated then chromatographed on silica gel using ethyl acetate, followed by 5-10% (2M NH3 in MeOH) in dichloromethane as eluent to give the desired 6-nitro-1-(3-(pyrrolidin-1-yl)propyl)-1,2,3,4-tetrahydroquinoline (270 mg, 0.933 mmol, 56.6% yield). 1H NMR (DMSO-d6) δ 7.87 (dd, J=9.3, 2.7 Hz, 1H), 7.77 (d, J=2.7 Hz, 1H), 6.70 (d, J=9.3 Hz, 1H), 3.46-3.38 (m, 4H), 2.74 (t, J=6 Hz, 2H), 2.43-2.38 (m, 6H), 1.86-1.82 (m, 2H), 1.74-1.67 (m, 6H).

Provenance & Evidence