Dimethylformamide → 5,6-Dihydro-1-methyl-5-oxo-1,6-naphthyridin-1-ium monoiodide

Participants

Reaction Conditions

Reaction Steps

A suspension of 5.85 g (40 mmol) of 1,6-naphthyridin-5(6H)-one (3), 10 mL of iodomethane, and 50 mL of anhydrous N,N-dimethylformamide is stirred at 25° C. for 19 hours. The suspension is treated with an additional 4 mL of iodomethane, stirred for 24 hours more, and poured slowly into 100 mL of stirring acetone. The solids are collected by filtration, washed with acetone, and dried to leave 10.54 g of pure product, mp 240°-244° C. The filtrate is concentrated in vacuo to give a solid residue that is triturated with 2-propanol and further processed to give 0.78 g of a second crop, mp 235°-240° C.

Provenance & Evidence