Acetic Anhydride → 1-[(Dimethylamino)carbonyl]-4-methoxy-6-(4-methoxybenzyl)-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridin-3-yl acetate

Participants

Reaction Conditions

Reaction Steps

4-methoxy-6-(4-methoxybenzyl)-N,N-dimethyl-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxamide 2-oxide (10.3 g) was dissolved in 30 ml acetic anhydride and transferred to a 50 mL heavy walled pressure flask and sealed. The reaction was heated in a 100° C. oil bath overnight. The reaction was concentrated in vacuo. The remaining oil was dissolved in 5 mL EtOAc and purified on an Isco automated system affixed with a Biotage Flash 40 (L) (120 g silica) cartridge eluted with 0-10% MeOH in EtOAc over 20 minutes and hold at 10% for 40 minutes. The product eluted pure by HPLC/MS and NMR.

Provenance & Evidence