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

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Reaction Steps

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.

Provenance & Evidence