4-Nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine → 3-phenyl-2,3-dihydro4H-1,4-benzoxazin-4-ylamine

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Reaction Steps

A slurry of lithium aluminum hydride (4.9 g, 130.5 mmol) in ethyl ether (100 mL) is stirred at ice bath temperature under an argon atmosphere. A solution of 4-nitroso-3-phenyl-3,4-dihydro-2H-1,4-benzoxazine in ethyl ether (300 mL) is added dropwise over 1 h. The mixture is removed from the ice bath and allowed to stir for 18 h. Water (50 mL) is slowly added forming solids. The solids are collected by filtration and washed with ethyl ether. The resulting filtrates are combined and washed three times with water (200 mL), dried over magnesium sulfate, and concentrated to give 8.7g (61%) of 3-phenyl-2,3-dihydro-4H-1,4-benzoxazin-4-ylamine.

Provenance & Evidence