N-[(4-chlorophenyl)methyl]-6-iodo-7-methoxy-1-methyl-4-oxo-1,8-naphthyridine-3-carboxamide → N-[(4-chlorophenyl)methyl]-1-methyl-4,7-dioxo-8H-1,8-naphthyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

N-(4-Chlorobenzyl)-6-iodo-7-methoxy-1-methyl-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxamide (150 mg) is mixed with pyridine hydrochloride (1.50 g). The resulting solid is heated at 200° C. for 1 h, then cooled to room temperature and washed with MeOH. The residue is then dissolved in CH2Cl2, washed with 1N HCl, brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product is purified by silica gel chromatography (CH2Cl2/MeOH 19/1, 9/1) to afford 60 mg (56%) of N-(4-chlorobenzyl)-1-methyl-4,7-dioxo-1,4,7,8-tetrahydro[1,8]naphthyridine-3-carboxamide. Physical characteristics are as follows: 1H NMR (DMSO-d6) δ8.85, 8.44, 7.42-7.33, 6.82, 4.55, 3.92; IR (diffuse reflectance) 3044, 2350, 2318, 1941, 1908, 1679, 1645, 1627, 1553, 1524, 1504, 1466, 803, 672, 656, cm−1.

Provenance & Evidence