Water → 7-bromo-1H,2H,3H-pyrido[2,3-b][1,4]oxazine

7-bromo-1H-pyrido[2,3-b][1,4]oxazin-2-one (1.3 g, 5.68 mmol) was dissolved in 30 ml of anhydrous tetrahydrofuran under nitrogen atmosphere and the mixture was cooled to 0□. 1.0M Lithium aluminum hydride dissolved in tetrahydrofuran (6.90 ml, 6.82 mmol) was added thereto dropwise and then stirred for 30 minutes. To the reaction mixture, water (0.3 ml), 10% sodium hydroxide (0.6 ml) and water (0.9 ml) were added dropwise in this order and then stirred vigorously at room temperature for 1 hour. The resulting solid was filtered and washed with excess ethyl acetate. The filtrate was washed with water and saturated saline solution, dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure to obtain 7-bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine as white solid (629 mg, 52%).

1. temperaturethe mixture was cooled to 0□
2. additionwas added
3. stirringstirred vigorously at room temperature for 1 hour
4. filtrationThe resulting solid was filtered
5. washwashed with excess ethyl acetate
6. washThe filtrate was washed with water and saturated saline solution
7. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
8. filtrationfiltered
9. customevaporated under reduced pressure

ORD record

ord-2adf56806f464cad92a866dce50939e7

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394792B2