Dichloromethane → HCID 86732794, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-chloro-1-ethyl-6,7-dihydroxy-4-oxo-1,4-dihydrocinnoline-3-carboxylic acid (1.46 g, 5.13 mmol) in N,N-dimethylformamide (DMF) (20 mL) was added potassium carbonate (1.772 g, 12.82 mmol) followed by 1-(chloromethyl)-4-methoxybenzene (1.392 mL, 10.26 mmol). The mixture was heated at 50° C. for 12 h, extracted with ethyl acetate and washed with water, brine, dried over magnesium sulfate. The solvent was removed under vacuum and the residue was chromatographed on ISCO silica column eluting with 0-10% methanol:dichloromethane to afford 4-methoxybenzyl 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carboxylate (1.4 g, 2.170 mmol, 42.3% yield). LCMS: (M+H)+: 645.2

Provenance & Evidence