Acetyl chloride → HCID 19093737, compound

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Reaction Steps

A mixture of 4'-[(5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]biphenyl-2-sulphonamide (250 mg), acetyl chloride (2 ml) and acetic acid (1 ml) was heated at reflux for 4 hours. The mixture was then concentrated by evaporation and the residue was purified by repeated precipitation from ethanol solution by the addition of ether to give N-acetyl-4'-[(5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-1-yl)methyl]biphenyl-2-sulphonamide hydrochloride as an amorphous solid (153 mg); NMR (d6 -DMSO): 1.27(t, 3H), 1.31(t, 2H), 1.69(s, 3H), 2.99(q, 2H), 3.36(q, 2H), 5.63(s, 2H), 6.98(d, 1H), 7.2-7.4(complex m, 5H), 7.5-7.8(m, 3H), 8.06(dd, 1H), 8.40(d, 1H), 11.53(s, 1H); mass spectrum (+ve FAB, methanol/NBA): 490 (M+H)+ ; microanalysis, found: C, 59.9; H, 5.4; N, 7.7%; C27H27N3O4S.HCl.H2O requires: C, 59.6; H, 5.5; N, 7.7%.

Provenance & Evidence