Water → 1H-Pyrido[3,4-b][1,4]oxazin-2(3H)-one

4-amino-3-pyridinol (650 mg, 5.904 mmol) was dissolved in anhydrous N,N-dimethyl formamide (15 ml) under nitrogen atmosphere, and chloroacetyl chloride (0.52 ml, 6.494 mmol) solution was added thereto dropwise at room temperature and then stirred for 30 minutes. Then, potassium carbonate (2.0 g, 14.760 mmol) was added thereto dropwise at room temperature, and the reaction mixture was heated at 100□ for 18 hours. The reaction mixture was cooled to room temperature and water was added to quench the reaction. The organic layer was extracted with ethyl acetate and the combined organic layer was washed with water and saturated saline solution, dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure to obtain white solid. The obtained white solid was recrystallized from ethyl acetate and n-hexane to obtain white solid (520 mg, 59%).

1. temperaturedropwise at room temperature, and the reaction mixture was heated at 100□ for 18 hours
2. temperatureThe reaction mixture was cooled to room temperature
3. customto quench
4. customthe reaction
5. extractionThe organic layer was extracted with ethyl acetate
6. washthe combined organic layer was washed with water and saturated saline solution
7. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
8. filtrationfiltered
9. customevaporated under reduced pressure
10. customto obtain white solid
11. customThe obtained white solid was recrystallized from ethyl acetate and n-hexane

ORD record

ord-12f529fa66fc4cc0a1ac08fd0e6313e5

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394792B2