1-Hydroxybenzotriazole → HCID 59327639, compound

Participants

Reaction Steps

To a solution of 2-(4-chlorophenyl)-2-methylpropanoic acid (10.0 g, 50.5 mmol) in dry acetonitrile (100 ml) and dry N,N-dimethylformamide (25 ml) at room temperature was added 1-hydroxybenzotriazole (HOBt, 8.2 g, 61 mmol), followed by ethyl dimethylaminopropylcarbodimide hydrochloride (EDC, 11.65 g, 61 mmol). The mixture was stirred at room temperature for 12 hours, at which time all the starting acid had been consumed as shown by TLC (30% ethyl acetae:hexanes) analysis. The reaction mixture was cooled to 0° C., and slowly added to a solution of hydrazine hydrate at 0° C. (4.8 ml, 100 mmol) in acetonitrile (50 ml). The mixture was stirred at 0° C. for 1 hour, then warmed to room temperature for 3 hours. Solvent was removed under reduced pressure, and the residue diluted with ethyl acetate, which was washed with water (2×), then brine. The organic phase was separated, and solvent removed under reduced pressure to provide 2-(4-chlorophenyl)-2-methylpropanehydrazide (9.64 g, 90%) as a white solid. LCMS (CI) shows M+H 213.

Provenance & Evidence