Hydrazine → Ethyl 2-hydrazinylnicotinate

Temperatur

60 °C

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.

1. customwas not consumed
2. temperatureAfter cooling to room temperature
3. concentrationthe reaction mixture was concentrated in vacuo
4. customThe obtained residue was triturated with MeOH (35 mL)
5. customthe insoluble white solid was removed by filtration
6. concentrationThe methanol solution was concentrated in vacuo
7. customto yield a fluffy yellow solid which
8. customwas triturated in diethylether

ORD-Eintrag

ord-cecee5ee1fc8460fb19765fa07c64279

Quelldatensatz

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08324241B2