Hydrazine → HCID 53404568, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 2-chloronicotinate (10.0 g, 53.9 mmol) and anhydrous hydrazine (2.04 g, 63.8 mmol) in anhydrous 1,4-dioxane (200 mL) was stirred at 60° C. for 2 h. Analysis by LC/MS indicated the starting material was not consumed. Additional amount hydrazine (2.04 g, 63.8 mmol) was added and the reaction mixture was stirred at 60° C. overnight. After cooling to room temperature, the reaction mixture was concentrated in vacuo. The obtained residue was triturated with MeOH (35 mL), the insoluble white solid was removed by filtration and discarded. The methanol solution was concentrated in vacuo to yield a fluffy yellow solid which was triturated in diethylether to yield the title compound as an orange solid (5.4 g, 55%). HPLC/MS (Method D): retention time=1.46 min, [M+H]+=182.3.

Provenance & Evidence