p-Toluenesulfonic acid → 4-hydroxy-N,N,2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide

Participants

Reaction Conditions

Reaction Steps

A solution of 6-(4-methoxybenzyl)-4-methoxy-N,N, 2-trimethyl-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridine-1-carboxamide (0.18 g, 0.45 mmol) in toluene (about 3 mL) was treated with p-toluene sulfonic acid (0.34 g, 1.8 mmol). The mixture was heated to 110° C. for 4 hours, then cooled and concentrated under vacuum. The residue was partitioned between water and EtOAc, the aqueous layer concentrated, and the residue purified by reverse phase chromatography to give the title product.

Provenance & Evidence