Dicyclohexylcarbodiimide → HCID 66616066, compound

Participants

Reaction Steps

At 0° C., to a suspension of 3-cyanobenzoic acid (0.62 g, 4.2 mmol) in dichloromethane (15 mL) is added THE dropwise until the system became homogenous, which is followed by the addition of 1-hydroxybenzotriazole (0.57 g, 4.2 mmol) and dicyclohexylcarbodiimide (0.87 g, 4.2 mmol). The mixture is brought to room temperature slowly and stirred for 0.5 h. To the mixture, methyl 4-hydrazinobenzoate (0.63 g, 3.8 mmol) is added and the mixture is stirred for 2 hr. The precipitate is then removed by filtration and washed with dichloromethane. The filtrate is washed with water and brine, dried over anhydrous Na2SO4, which is discarded later. The crude product obtained after the removal of the solvent is separated by column chromatography (silica gel, 1:19 ethyl acetate-dichloromethane) to provide the intermediate, methyl 4-[2-(3-cyanobenzoyl)hydrazino]benzoate (0.68 g, 61%). MS (ES+) m/z: 296.

Provenance & Evidence