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 organic phase is collected, dried over MgSO4, filtered and evaporated to give the title compound (24 g, 40% purity) as a yellow wax; LC-MS: tR=0.82 min; [M+H]+=285.10.

Provenance & Evidence