Sodium Methoxide → Sodium 1-(ethoxycarbonyl)-6-(4-fluorobenzyl)-3,5-dioxo-2,3,5,6,7,8-hexahydro-2,6-naphthyridin-4-olate

Participants

Reaction Steps

To ethyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate 2-oxide (2.3 gm, 6.38 mmol) in neat acetic anhydride (24 mL) was stirred under nitrogen at 100° C. for 1 hour. The reaction was concentrated to an oil under reduced pressure and dry methanol (20 mL) was added followed by a methanolic sodium methoxide solution (30% by wt) (4.54 mL, 25.2 mmol). The reaction was stirred at room temperature for 1 hour. The reaction was then concentrated to an oil under reduced pressure and crystallized from a small amount of methanol (˜5 mL). The crystals were collected by filtration, washed an additional 10 mL of methanol and dried in vacuo to give the desired product.

Provenance & Evidence