Benzoyl Peroxide → 2-Chloromethyl-1,6-naphthyridine

Participants

Reaction Steps

To a solution of 2-methyl-1,6-naphthyridine (E. M. Hawes, J. Heteroc. Chem. 11(2), 151 (1974)) (3.8 g) in CCl4 (230 mL) were added N-chlorosuccinimide (4.2 g) and benzoylperoxide (320 mg). The mixture was brought to reflux with two 150-watt spotlights and irradiated for 4 hr. The mixture was then cooled to room temperature, evaporated to dryness, and chromatographed on flash silica gel using ethyl acetate:toluene (1:1) as eluant to give the title compound, 80% pure and used as is for the next step.

Provenance & Evidence