Water → 8-Chloro-2,3-dihydro-1H-pyrido[2,3-B][1,4]oxazine

8-chloro-1H-pyrido[2,3-b][1,4]oxazin-2-one (600 mg, 3.25 mmol) was dissolved in anhydrous tetrahydrofuran (16 ml) under nitrogen atmosphere, and then cooled to 0□. 1.0M Lithium aluminum hydride dissolved in tetrahydrofuran (6.5 ml, 6.50 mmol) was added thereto dropwise, and then stirred for 30 minutes. The reaction temperature was raised to room temperature and stirred for 1 hour. The reaction mixture was cooled to 0□ again, and water (0.26 ml), 10% sodium hydroxide solution (0.52 ml) and water (0.78 ml) were added thereto dropwise in this order, and then stirred vigorously at room temperature for 1 hour. The formed solid was filtered and washed with excess ethyl acetate.

1. temperaturecooled to 0□
2. additionwas added
3. stirringstirred for 1 hour
4. temperatureThe reaction mixture was cooled to 0□ again
5. stirringdropwise in this order, and then stirred vigorously at room temperature for 1 hour
6. filtrationThe formed solid was filtered
7. washwashed with excess ethyl acetate

ORD record

ord-ec825972028d462b9852b23d3056fc8d

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394792B2