Hydrazine hydrate (1:1) → C-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methylamine

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Reaction Steps

To a solution of 2-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-isoindole-1,3-dione (5.9 g, 18 mmol) in THF (248 mL) and ethanol (21 mL) at 0° C. was added hydrazine hydrate (6.7 g, 6.5 mL, 134 mmol) and the resulting mixture stirred at room temperature overnight. The mixture was then filtered and the filtrate diluted with HCl (1 N) and extracted with ethyl acetate. The combined organic extracts were then washed with HCl (1 N) and the aqueous layer made basic with NaOH (6 N). The aqueous layers were extracted with ethyl acetate and the combined organic layers washed with brine and dried over sodium sulfate. Concentration afforded the title compound (2.0 g, 54%) as a light yellow oil. MS: m/e=190.3 [M+H]+.

Provenance & Evidence