Tetrahydrofuran → Phenyl 2-(6-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate

Participants

Reaction Steps

Phenyl methyl(2-(6-nitro-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate (1.29 g, 3.49 mmol) was dissolved by stirring in ethanol (40 mL) and THF (30 mL) in a round bottom flask. The solution was stirred under an atmosphere of hydrogen for 6 h at room temperature. When TLC confirmed the reaction was completed, the mixture was filtered through celite, and the filtrate was concentrated. The resulting residue was chromatographed on silica gel eluting with ethyl acetate, giving a white/pink foam. Yield: 990 mg, 84%. 1H NMR (DMSO-d6) δ 7.36 (m, 2H), 7.20 (m, 1H), 7.01 (m, 2H); 6.91 (d, 1H, J=8.4 Hz), 6.43 (m, 2H), 4.87 (s, 2H), 4.11 and 4.03 (2m, 2H), 3.56 and 3.44 (2t, 2H, J=6.0 Hz), 2.99 and 2.87 (2s, 3H), 2.66 (m, 2H), 2.43 (m, 2H); ESI-MS (m/z, %): 362 (MNa+, 35), 340 (MH+, 100), 202 (44).

Provenance & Evidence