N-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-1-methyl-4-oxo-quinoline-3-carboxamide → N-(4-Chlorobenzyl)-6-(3-hydroxypropyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

Participants

Reaction Steps

A mixture of 0.50 g of N-(4-chlorobenzyl)-6-(3-hydroxy-1-propynyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide from Example No. 31 and 50 mg of 5% platinum on carbon catalyst in 20 mL of 1:1 THF-methanol is stirred under 1 atm hydrogen for 3 h, then filtered through diatomaceous earth. The filtrate is concentrated under reduced pressure and the residual solid flash chromatographed on silica gel using 4-5% methanol in dichloromethane to afford 0.45 g of the title compound as a yellow solid. Further purification is achieved by recrystallization of the solid from 15 mL of acetonitrile.

Provenance & Evidence