Methanol → 4-[1-(3-Amino-pyrazol-1-yl)-butyl]-benzoic acid methyl ester

Participants

Reaction Steps

The 4-[1-(3-nitro-pyrazol-1-yl)-butyl]-benzoic acid methyl ester (127 mg, 0.42 mmol) was dissolved in ethyl acetate (3 mL) and methanol (3 mL) was added. While stirring, a 50% slurry of raney nickel in water (500 μL) was added followed by hydrazine (150 μL). Immediate effervescence was observed. The reaction continued to stir and bubble for 30 min. The reaction was passed through a plug of celite and concentrated in vacuo to afford 4-[1-(3-amino-pyrazol-1-yl)-butyl]-benzoic acid methyl ester (108 mg, 94%) as a clear oil: ESI-LRMS m/e calcd for C15H19N3O2 [M+] 273.15, found 274.29 [M+H+], 547.43 [2M+H+].

Provenance & Evidence