Diethyl Ether → Ethyl 1-allyl-4-hydroxy-7-methyl-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Beteiligte Stoffe

Reaktionsschritte

To a solution of 2.88 g. (0.015 mole) of 2-allylamino-6-methylnicotinic acid, methyl ester in 50 ml. of anhydrous diethyl ether was added 1.12 g. (0.0075 mole) of ethyl malonyl chloride. The mixture was stirred at room temperature for 4 hours. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The residue was dissolved in 5 ml. of ethanol and this solution was added to a solution of 0.23 g. (0.01 g. atoms) of sodium in 20 ml. of ethanol. The mixture was stirred at room temperature for 5 minutes. The mixture was diluted with water and was acidified with glacial acetic acid. The mixture was extracted with diethyl ether and the ether layer was dried over magnesium sulfate, filtered and was acidified with an etheral hydrochloric acid solution. The mixture was filtered and the filtrate was evaporated. The residue was recrystallized from heptane to give 10 mg. of the title compound, m.p. 110°-112° C.

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