反应详情

To a suspension of 4-(4-methoxypyridin-2-yl)-2-nitrocinnamonitrile (308 mg) in ethanol (30 ml) was added tin (II) chloride dihydrate (1.41 g), and the mixture was refluxed for 30 minutes. Then to the solution was added hydrochloric acid (12N, 5 ml), and the mixture was refluxed for 6 hours. After cooling, the reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 150 g, 10% methanol in dichloromethane). The compound obtained was dissolved in ethyl acetate, and a solution of hydrogen chloride in 1,4-dioxane (4N, 1 ml) was added. The precipitate was collected by filtration and dried to give 2-amino-7-(4-methoxypyridin-2-yl)-quinoline dihydrochloride (77 mg).

1. temperaturethe mixture was refluxed for 30 minutes
2. temperaturethe mixture was refluxed for 6 hours
3. temperatureAfter cooling
4. extractionextracted with dichloromethane
5. washThe organic layer was washed with brine
6. dry with materialdried over sodium sulfate
7. customevaporated under reduced pressure
8. customThe residue was purified by column chromatography (silica gel 150 g, 10% methanol in dichloromethane)
9. customThe compound obtained
10. filtrationThe precipitate was collected by filtration
11. customdried