2,6-Lutidine → 8-Chloro-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridine-9-carbaldehyde

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Reaction Steps

To a solution of 8-chloro-4,6-dimethyl-9-vinylbenzo[c][2,7]naphthyridin-5(6H)-one (600 mg, 2.107 mmol), osmium tetroxide (2.5% in 2-methyl-2-propanol) (0.794 mL, 0.063 mmol), and 2,6-dimethylpyridine (0.491 mL, 4.21 mmol) in 1,4-dioxane (30 mL) and water (30 mL) cooled to 0° C. was added sodium periodate (1803 mg, 8.43 mmol). The mixture was warmed to room temperature and stirred for 3 h. The mixture was diluted with ethyl acetate and filtered through diatomaceous earth (Celite®). The organic layer was concentrated under reduced pressure to afford a brown solid. The solid was washed with hexane (3×20 mL) and dried under vacuum to afford 8-chloro-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridine-9-carbaldehyde 0.6 g, 2.107 mmol, 84% yield) as a gummy brown solid. LC/MS (ESI) m/e 287.0 [(M+H)+, calcd for C15H12ClN2O2, 287.1]; LC/MS retention time (method B): tR=2.03 min.

Provenance & Evidence