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B) 7-Chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one A mixture of <strong>[76629-11-3]N-(6-chloropyridin-2-yl)-beta-alanine</strong> (40 g) and Eaton's Reagent (600 mL) was stirred at 75C for 3 hours. The reaction mixture was poured to ice water and basified to pH = 10 with sodium hydroxide, followed by extraction with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound. MS: [M+H]+ 182.8.
7-chloro-1-(3,4-dimethoxybenzoyl)-2,3-dihydro-1,8-naphthyridin-4(1H)-one trifluoroacetic acid salt[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
28 mg
C) 7-Chloro-1-(3,4-dimethoxybenzoyl)-2,3-dihydro-1,8-naphthyridin-4(1H)-one trifluoroacetic acid salt To a solution of <strong>[76629-10-2]7-chloro-2,3-dihydro-1,8-naphthyridin-4(1H)-one</strong> (0.6 g) in THF (30 mL), a 1 M solution of lithium bis(trimethylsilyl)amide in hexane (3.3 mL) was added at-75C to -70C. The reaction mixture was stirred at the same temperature as above for 30 minutes, and then, a solution of 3,4-dimethoxybenzoyl chloride (0.8 g) in THF (5 mL) was added thereto over 30 minutes. The temperature of the reaction mixture was raised to room temperature, and the reaction mixture was poured to water, followed by extraction with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was purified by reverse-phase HPLC to obtain the title compound (28 mg). MS: [M+H]+ 346.9.
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