Methyl iodide → N-(4-Chlorobenzyl)-6-(hydroxymethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

Participants

Reaction Steps

A solution of N-(4-chlorobenzyl)-4-hydroxy-6-(hydroxymethyl)-3-quinolinecarboxamide from Preparation No. 3 (300 mg,), K2CO3 (485.1 mg), and CH3I (0.11 mL) in 4 mL anhydrous DMF is heated at 90° C. for 3 hours. The reaction is cooled to room temperature and diluted with H2O to dissolve any salts and precipitate the product. The crude product is adsorbed onto silica and chromatographed eluting with 3% MeOH in CH2Cl2. Fractions homogenous by TLC are combined and condensed to afford 154.2 mg (49%) of the title compound as a white solid.

Provenance & Evidence