Water → 5-methyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine

5-methyl-1H-pyrido[2,3-b][1,4]oxazin-2-one (424 mg, 2.58 mmol) was dissolved in 20 ml of anhydrous tetrahydrofuran under nitrogen atmosphere, and then cooled to 0□. 1.0M Lithium aluminum hydride dissolved in tetrahydrofuran (5.16 ml, 5.16 mmol) was added thereto dropwise and then stirred for 30 minutes. The reaction temperature was raised to room temperature and then stirred for 1 hour. The reaction mixture was cooled to 0□ again and water (0.2 ml), 10% sodium hydroxide solution (0.4 ml) and water (0.6 ml) were added thereto dropwise in this order, and stirred vigorously at room temperature for 1 hour. The formed precipitate 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 5-methyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine as white solid (100 mg, 26% in two steps).

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 stirred vigorously at room temperature for 1 hour
6. filtrationThe formed precipitate was filtered
7. washwashed with excess ethyl acetate
8. washThe filtrate was washed with water and saturated saline solution
9. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
10. filtrationfiltered
11. customevaporated under reduced pressure

ORDレコード

ord-f985395a10f24e32a0d6e1345ac67f6a

出典データセット

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08394792B2