Hydrazine → 4-(3-Bromo-2-hydrazinylpyridin-4-yl)benzonitrile

Temperature

80 °C

To a suspension of 4-(3-bromo-2-chloropyridin-4-yl)benzonitrile (0.59 g, 2.02 mmol) in dioxane (7 mL) at room temperature was added anhydrous hydrazine (1 mL). The resulting mixture was stirred at 80° C. for 2 h. Analysis by HPLC/MS indicated the reaction was not complete. Additional anhydrous hydrazine (1 mL) was added, and the reaction mixture was stirred at 90° C. for 5 h more. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Water was added to the residue, and the resulting suspension was sonicated for 5 min. The resulting slurry was filtered, and the collected solid was washed with water (10 mL×2), then dried in a 45° C. vacuum oven for 16 h to afford 510 mg of the title compound as a beige solid. HPLC/MS: retention time=1.74 min, [M+H]+=289.

1. stirringthe reaction mixture was stirred at 90° C. for 5 h more
2. temperatureAfter cooling to room temperature
3. concentrationthe reaction mixture was concentrated under reduced pressure
4. additionWater was added to the residue
5. customthe resulting suspension was sonicated for 5 min
6. filtrationThe resulting slurry was filtered
7. washthe collected solid was washed with water (10 mL×2)
8. customdried in a 45° C. vacuum oven for 16 h

ORD record

ord-aa721552abe14eaa9f81682248abccea

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07572808B2