Hydrazine hydrate (1:1) → 1041853-14-8

Temperature

80 °C

An open 250 mL round bottom flask was charged with 1-bromo-2-(2-methoxyethoxy)-4-nitrobenzene (Method 10) (5 g, 18.11 mmol), 5 wt % FeCl3 on SiO2 (17.6 g, 5.43 mmol), activated carbon (10 g), and 100 mL MeOH. This resulting mixture was heated with stirring to 80° C. Hydrazine monohydrate (10.6 mL, 217 mmol) was then carefully added to the reaction mixture. After complete addition of the hydrazine monohydrate, the reaction mixture was stirred at 80° C. for an additional 40 min. The reaction was then allowed to cool to rt and filtered through a bed of Celite. The filter cake was washed with MeOH (˜150 mL) and EtOAc (˜150 mL). The resulting filtrate was conc in vacuo to give the title compound which was used without further purification (3.16 g, 71%) m/z: 247.

1. temperatureThis resulting mixture was heated
2. stirringthe reaction mixture was stirred at 80° C. for an additional 40 min
3. temperatureto cool to rt
4. filtrationfiltered through a bed of Celite
5. washThe filter cake was washed with MeOH (˜150 mL) and EtOAc (˜150 mL)

ORD record

ord-6a4d6b0e383d48d9b4b2dc95f0832c96

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07723337B2