Sodium hydride → 7-Methyl-1, 6-naphthyridine-5 (6H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 272.3 mg (2 mmol) of 2-methylnicotinamide (2) and 0.34 mL (2.2 mmol) of 95% N,N-dimethylacetamide, dimethylacetal is heated at 50° C. for 1.5 hours, then a vacuum is applied for 1 hour with heating as described above. The oil is diluted with 2 mL of dry N,N-dimethylacetamide, treated with 96 mg of 60% sodium hydride, and heated at 80° C. for 2.5 hours. The solution is treated with 70 mg more of 60% sodium hydride, heated for an addition 4.5 hours, then quenched with excess acetic acid. The mixture is concentrated at 2 mm/70° C. to leave a residual solid that is triturated in hot chloroform, then filtered through a pad of silica gel (230-400 mesh). The pad is eluted with chloroform, then acetone to collect the product. The filtrate is concentrated to a solid that is dissolved in a minimum volume of hot water. The solution is stored at 5° C. for 2 weeks, and the precipitated solids are collected by filtration, washed well with propanol, and dried to give 73 mg of pure product, mp 244°-245° C.

Provenance & Evidence