2,3,4,5-Tetrahydro-1,5-benzoxazepine → 5-Nitroso-2,3,4,5-tetrahydro-1,5-benzoxazepine

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Reaction Steps

To a stirred, cold slurry of 2,3,4,5-tetrahydro-1,5-benzoxazepine (13.72 g, 91.96 mmol) in 2N aqueous HCl (105 mL) was added dropwise a solution of NaNO2 (7.30 g, 105.75 mmol) in H2O (16 mL) and stirred at room temperature for 2 hrs. The mixture was taken up in H2O (800 mL), extracted with ether (3×200 mL), dried over MgSO4, and stripped of the solvent under reduced pressure to yield 15.59 g (95%) of 5-nitroso-2,3,4,5-tetrahydro-1,5-benzoxazepine as a tan powder. (M+H)+ 178.

Provenance & Evidence