Hydrochloric Acid → 1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-amine

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Reaction Steps

To a solution of 1-(3-trifluoromethyl-phenyl)-4,5-dihydro-1H-pyrazol-3-ylamine hydrochloride salt (200 mg, 0.88 mmol) (Example 3A) in dioxane (50 mL) was added triethylamine (0.069 mL, 0.88 mmol) followed by 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) (200 mg, 0.88 mmol). The mixture was stirred at room temperature for 24 h and then poured onto dichloromethane. 2N hydrochloric acid was added and the organics extracted with 2N hydrochloric acid (3×50 mL). The acid layer was basified with 10N potassium hydroxide and extracted with dichloromethane (3×50 mL). The combined organics were dried (Na2SO4), filtered and evaporated to dryness. The residue dissolved in diethyl ether and 1M hydrochloric acid in diethyl ether was added to form a brown solid which was collected and dried (171 mg, 86%). MS (ES) m/z: 228.1 [M+H].

Provenance & Evidence