Water → N-[(4-chlorophenyl)methyl]-1-(2-diethylaminoethyl)-8-fluoro-6-(3-hydroxyprop-1-ynyl)-4-oxo-quinoline-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of N-(4-chlorobenzyl)-8-fluoro-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Preparation No. 15 (0.96 g) is dissolved in DMF (7 mL), and K2CO3 (1.38 g) and 2-bromo-N,N-diethylethylamine hydrobromide (1.30 g) are added. The reaction mixture is heated to 95° C. for 16. Water is added and an oily solid formed, which is isolated by decanting the liquid. Column chromatography (elution with 1-3% MeOH/CHCl3) gave 0.373 g of the title compound which is crystallized from ethyl acetate to give 0.163 g of a solid.

Provenance & Evidence