Potassium Carbonate → HCID 86732763, compound

Participants

Reaction Conditions

Reaction Steps

To a red suspension of 5-chloro-1-ethyl-6,7-dihydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (12.2 g, 43.0 mmol), K2CO3 (23.78 g, 172 mmol) and KI (0.714 g, 4.30 mmol) in N,N-Dimethylformamide (DMF) (200 mL) at r.t. was added 1-(chloromethyl)-4-methoxybenzene (19.26 mL, 142 mmol). The mixture was heated at 90° C. for 4 h. After cooling, the mixture was concentrated and partitioned between water (200 mL) and DCM (200 mL), and extracted with DCM (150 mL) twice. The organic layers were combined, dried and concentrated. The crude product was purified twice through column chromatography eluting with EtOAc/hexanes (0-100%) to afford pure 4-methoxybenzyl 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylate (14 g, 20.65 mmol, 48.0% yield) as a white solid. LCMS: (M+H)+: 644.1.

Provenance & Evidence