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

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Reaction Steps

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%).

Provenance & Evidence