Hydrazine → 4-Benzyloxy-3-ethyl-5-methyl-benzoic acid hydrazide

Participants

Reaction Steps

To a solution of 4-benzyloxy-3-ethyl-3-methyl-benzoic acid (8.3 g, 30.7 mmol) in DCM (300 mL) is added DIPEA (10.7 mL) and the mixture is cooled to 0° C. before PyBOP (14.5 g, 33.8 mmol) is added. After 10 min, a solution of 1M hydrazine in THF (100 mL) is added dropwise and the mixture is slowly warmed to rt during 2 h. The reaction mixture is then washed with sat. aq. NaHCO3 followed by brine. The org. phase is collected, dried over MgSO4, filtered and evaporated to give the title compound as a yellow wax (24 g, 40% purity). LC-MS: tR=0.82 min; [M+H]+=285.10.

Provenance & Evidence