Formaldehyde → N-(diethylaminomethyl)-1-(4-fluorophenyl)-4-oxo-7-(4-pyridyl)quinoline-3-carboxamide

Participants

Reaction Steps

A mixture of 2.2 g 1-(4-fluorophenyl)-1,4-di -hydro-4-oxo-7-(4-pyridinyl)-3-quinolinecarboxamide (Example 1h) and molar excess amounts of formaldehyde and diethylamine in 100 ml ethanol was heated at reflux for two days. The ethanol was removed and the residual product chromatographed on silica gel. The column was eluted with 10% isopropyl alcohol in chloroform; starting material was eluted first followed by fractions containing the desired N-diethylaminomethyl compound. The latter was recrystallized from ethyl acetate to give 0.9 g N-(diethylaminomethyl)-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-7-(4-pyridinyl)-3-quinolinecarboxamide, m.p. 193195° C.

Provenance & Evidence