Methyl iodide → N-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-1-methyl-4-oxo-quinoline-3-carboxamide

Participants

Reaction Steps

A suspension of 6.90 g of N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Preparation No. 4, 10.4 g of potassium carbonate, and 2.3 mL of methyl iodide in 40 mL of DMF is stirred at 90° C. for 4 hours, then cooled and diluted with 350 mL of water. The resulting solid is filtered, washed well with water, and dried under vacuum. Flash chromatography of the solid on silica using 3-5% methanol in dichloromethane provides 6.02 g of the title compound as a solid.

Provenance & Evidence