Chloroacetyl chloride → 5-methyl-1H-pyrido[2,3-b][1,4]oxazin-2-one

3-amino-5-methyl-pyridin-2-ol (1.32 g, 10.6 mmol) was dissolved in 50 ml of anhydrous N,N-dimethyl formamide under nitrogen atmosphere, and chloroacetyl chloride solution (1.02 ml, 12.72 mmol) was added thereto dropwise at room temperature. After stirring for 30 minutes, potassium carbonate (3.7 g, 26.5 mmol) was added thereto dropwise at room temperature, and the reaction mixture was heated to 100□ and then stirred for 18 hours. The reaction mixture was cooled to room temperature and the reaction was quenched by adding water. 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 straw yellow solid (424 mg). The resulting solid was used in the next step without further purification.

1. customdropwise at room temperature
2. stirringstirred for 18 hours
3. temperatureThe reaction mixture was cooled to room temperature
4. customthe reaction was quenched
5. additionby adding water
6. extractionThe organic layer was extracted with ethyl acetate
7. washthe combined organic layer was washed with water and saturated saline solution
8. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
9. filtrationfiltered
10. customevaporated under reduced pressure

ORD record

ord-07ce11b96d2c4160bfc8bc5afd657df0

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394792B2