Dichloromethane → N-[(4-chlorophenyl)methyl]-1-(2-hydroxyethyl)-6-(3-hydroxyprop-1-ynyl)-4-oxo-quinoline-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a flask containing N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Preparation No. 4 (0.37 g) is added potassium carbonate (2.75 g) and bromoethanol (0.71 mL). The flask is tightly capped and heated to 100° C. After 4 hours the reaction is cooled to room temperature and partioned between dichloromethane containing methanol and water. The organic layer is washed with two additional portions of water, brine, dried and concentrated under reduced pressure. The residue is adsorbed onto silica and chromatographed on silica eluting with 2% to 10% methanol in dichloromethane to afford 0.09 g of the title compound as a white solid.

Provenance & Evidence