2-Chloro-5-((2,2-dimethyl-1-oxopropyl)amino)-beta-hydroxy-4-pyridine propanoic acid, 1,1-dimethylethyl ester → 6-Chloro-1,7-naphthyridin-2(1H)-one

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Reaction Steps

A solution of 4.63 g (13 mmoles) of 2-chloro-5-((2,2-dimethyl-1-oxopropyl)amino)-β-hydroxy-4-pyridine propanoic acid, 1,1-dimethylethyl ester in 70 ml of dioxane and 30 ml of 3N HCl in water was warmed at reflux for a period of 4 hours. The solution was diluted with 100 ml of water and cooled to give a white precipitate. The crystals were filtered, washed with water and dried in a vacuum oven to give 2.18 g (93% of theoretical) of the above-captioned compound having a melting point of 304°-306° C. The carbon, hydrogen and nitrogen content calculated for C8H5ClN2O is C, 53.20; H, 2.79; and N, 15.52 percent by weight which compares to that actually found upon analysis of C, 53.55; H, 2.79; and N, 15.47.

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