HCID 53392179, compound → HCID 53392183, compound

Participants

Reaction Steps

A suspension of 1-(2-(1-methylpyrrolidin-2-yl)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (2.25 g, 7.42 mmol) and palladium on activated carbon (10%, 100 mg, 0.09 mmol) in 50 mL ethanol was stirred under a balloon of hydrogen for 2 days. The suspension was filtered through a pad of celite. The filter pad was rinsed with 50 mL ethanol and the filtrate was concentrated to give a viscous oil. The crude product was subjected to Biotage flash chromatography on silica gel using 0-5% 2M NH3 in MeOH/CH2Cl2 to give a yellow foam (1.48 g, 72.9%). 1H-NMR (CDCl3) δ: 6.82 (d, J=8.4 Hz, 1H), 6.55 (dd, J=3.0, 8.4 Hz, 1H), 6.52 (d, J=3.0 Hz, 1H), 4.09-3.99 (m, 1H), 3.86-3.76 (m, 1H), 3.54 (br s, 2H), 3.04-3.01 (m, 1H), 2.81-2.76 (m, 2H), 2.61-2.56 (m, 2H), 2.29 (s, 3H), 2.17-1.60 (m, 8H).

Provenance & Evidence