Hydrochloric Acid → Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Participants

Reaction Steps

A 2M solution of NaOEt in EtOH (5.87 mL, 11.74 mmol) was added to a solution of ethyl 3-[(3-ethoxy-3-oxopropanoyl)amino]-5-(4-fluorobenzyl)pyridine-2-carboxylate (2.28 g, 5.87 mmol) in EtOH (23 mL) and the mixture was stirred at rt for 1 h. The mixture was neutralized with conc. HCl and concentrated in vacuo. Trituration of the resulting material with a mixture of EtOH and 1:1 brine/water followed by filtration afforded the product as a beige solid: 1H NMR (d6-DMSO) δ 11.54 (1H, br s), 8.54 (1H, d, J=1.4 Hz), 7.44 (1H, s), 7.32 (2H, dd, J=8, 6 Hz), 7.17 (2H, t, J˜9 Hz), 4.23 (2H, q, J=7 Hz), 4.12 (2H, s), 1.26 (3H, t, J=7 Hz); HRMS calcd for C18H15FN2O4+H+: 343.1094. Found: 343.1088.

Provenance & Evidence