5,7-diethyl-1-(4-nitrobenzyl)-1,6-naphthyridin-2(1H)-one → 1-(4-aminobenzyl)-5,7-diethyl-1,6-naphthyridin-2(1H)-one

Participants

Reaction Steps

A solution of compound B (16.0 g) in THF (200 ml) was cataltically hydrogenated over platinum (IV) oxide (320 mg) at one atmosphere for 3 hours. The catalyst was removed by filtration and the solvent was removed by evaporation to give 1-(4-aminobenzyl)-5,7-diethyl-1,6-naphthyridin-2(1H)-one (C) as an off white solid (14.5 g), m.p. 164°-165° C.; NMR (d6 -DMSO): 1.85(t, 3H), 1.2(t, 3H), 2.72(q, 2H), 3.03(q, 2H), 5.1(s, 2H), 5.28(s, 2H), 6.48(d, 2H), 6.66(d, 1H), 6.94(d, 2H), 7.14(s, 1H), 8.16(d, 1H); mass spectrum (+ve FAB, MeOH/DMSO/NBA): 308 (M+H)+ ; microanalysis, found: C, 74.0; H, 6.9; N, 13.1%; C19H21N3O requires C, 74.2; H, 6.9; N, 13.1 %.

Provenance & Evidence