Dichloromethane → HCID 86732767, compound

Participants

Reaction Steps

To a solution of 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydro quinoline-3-carbaldehyde (21.3 g, 34.4 mmol) in 1,2-Dichloroethane (DCE) (200 mL) was added pyrrolidine (3.13 mL, 37.8 mmol) and sodium triacetoxyborohydride (10.93 g, 51.6 mmol). The mixture was stirred at r.t. for 3 h. Then reaction mixture was concentrated, partitioned between DCM and brine, and extracted with DCM twice. The combined organic extracts were dried over sodium sulfate and the solvent was removed in vacuo. The crude product was then purified through normal phase chromatography (CombiFlash Rf), eluting with [DCM/MeOH/NH4OH (v:v:v=80:20:2)]:DCM (0% to 60%) to afford 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-3-(pyrrolidin-1-ylmethyl)quinolin-4(1H)-one (17 g, 30.2 mmol, 88% yield) as a light yellow solid. LCMS: (M+H)+: 563.2.

Provenance & Evidence