Sodium Hydroxide → 5-(Benzoxazol-2-yl)-1-(tetrahydropyran-4-yl)benzotriazole

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Reaction Conditions

Reaction Steps

To a solution of 5-(benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)aminoaniline (see Working Example 20-2) (0.35 g, 1.13 mmol) in concentrated hydrochloric acid (2 mL) was added dropwise an aqueous solution containing sodium nitrite (0.09 g, 1.24 mmol) with cooling to 0° C. After stirring for 2 hours at room temperature, this was cooled to 0° C. and was made alkaline with 1N aqueous sodium hydroxide solution, then extracted with ethyl acetate, washed with water, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography to yield the title compound (0.17 g, 46.9% yield) as dark brown crystals.

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