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

Participants

Reaction Conditions

Reaction Steps

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Preparation No. 5 (0.616 g) is dissolved in DMF (4 mL), and K2CO3 (0.93 g, 6.72 mmol) and 2-bromo-N,N-diethylethylamine hydrobromide (0.88 g, 3.35 mmol) are added. The reaction mixture is heated to 90° C. for 16. The mixture is partitioned between CHCl3 and water. The organic layer is concentrated in vacuo to give an oil. Column chromatography (elution with 1-5% MeOH/CHCl3) gave 0.10 g of a brown oil. Crystallization from ethyl acetate/hexane gave 0.013 g of the title compound as a solid.

Provenance & Evidence