Ethanol → HCID 71272686, compound

Participants

Reaction Steps

A mixture of 5-((4-methoxybenzyl)oxy)-3-oxo-pentanenitrile (78 g, 334.4 mmol) and hydrazine hydrate (50 g, 1 mol) in EtOH (500 mL) was heated under reflux for 16 h. After cooling to RT, the solvent was removed in vacuo and the residue was partitioned between DCM (400 mL) and water (400 mL). The organic layer was separated and washed with brine, dried (Na2SO4), and then concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with 5% MeOH/DCM to afford 66 g (80%) of 5-(2-((4-methoxybenzyl)oxy)ethyl)-1H-pyrazol-3-amine as a yellow solid.

Provenance & Evidence