Hydrochloric Acid → 2-chloro-4-[3-(trifluoromethyl)-1H-pyrazol-1-yl]benzeneethanamine hydrochloride

Participants

Reaction Steps

To a cooled (0° C.) solution of sodium borohydride (238.6 mg, 6.28 mmol) in anhydrous tetrahydrofuran (8 mL) at 0° C. was added boron trifluoride diethyl etherate (1.13 g, 7.93 mmol) dropwise. The resultant solution was then stirred for 10 min at 0° C. and for 15 min at room temperature. A solution of 1-[3-chloro-4-(2-nitroethenyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole (i.e. the product of Step B; 420 mg, 1.32 mmol) in anhydrous tetrahydrofuran (5.2 mL) was added dropwise via cannula, and the resulting mixture was refluxed for 7.5 h and then allowed to cool to room temperature. Water (17 mL) was added dropwise, followed by 1 N hydrochloric acid (17 mL). The reaction mixture was concentrated under reduced pressure, and the residue was triturated with petroleum ether to afford the title compound (320 mg).

Provenance & Evidence