تفاعل #2281672

معادلة التفاعل

citric acid

3-oxo-1-cyclohexenyl 1-(ethylthiomethyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

triethylamine

acetone cyanohydrin

→

title compound

1-(ethylthiomethyl)-3-(2-hydroxy-6-oxo-1-cyclohexenecarbonyl)-1,8-naphthyridin-2(1H)-one

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   استخلاصthe mixture was extracted with dichloromethane
2. 2
   غسيلThe organic phase was washed with water
3. 3
   أخرىdried
4. 4
   تركيزconcentrated
5. 5
   أخرىThe residue was purified by column chromatography (ethyl acetate:n-hexane=1:4)

الإجراء التجريبي

2.97 g (8.3 mmol) of 3-oxo-1-cyclohexenyl 1-(ethylthiomethyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in dichloromethane (80 mL). 1.40 mL (10.0 mmol) of triethylamine and 0.77 g (9.1 mmol) of acetone cyanohydrin were added to the above solution, and the resulting mixture was stirred overnight at room temperature. The reaction mixture was poured into an aqueous solution of citric acid, and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried, and concentrated. The residue was purified by column chromatography (ethyl acetate:n-hexane=1:4), and thus 0.77 g of the title compound was obtained as pale orange-colored crystals (yield: 26%).

المصدر