Methanol → HCID 19093773, compound

Participants

Reaction Steps

2M Sodium hydroxide solution (3 ml) was added to a solution of methyl 4'-[(5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]biphenyl-2-carboxylate (A) (300 mg) in methanol (5 ml) and the mixture was heated at reflux for 2 hours. The mixture was cooled to ambient temperature and volatile material was removed by evaporation. The residue was dissolved in water and the solution adjusted to pH 5 with acetic acid. The precipitated solid was collected by filtration to give 4'-[(5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]biphenyl-2-carboxylic acid (100 mg) as a solid; m.p. 238°-240° C.; NMR (d6 -DMSO): 1.18(t, 3H), 1.26(t, 3H), 2.72(q, 2H), 3.60(q, 2H), 5.2(s, 2H), 6.70(d, 1H), 7.15(s, 1H), 7.23-7.71(m, 5H), 8.21(d, 1H), 12.65(broad s, 1H); mass spectrum (+ve FAB, methanol/NBA): 435 (M+Na)+, 413(M+H)+ ; microanalysis, found: C, 74.1; H, 5.6; N, 6.5%; C26H26N2O3.0.5.H2O requires; C, 74.0; H, 5.9; N, 6.6%.

Provenance & Evidence