Water → [1-(2-Nitrophenyl)ethylidene]hydrazine

Temperature

70 °C

To a solution of 2′-nitroacetophenone (8.26 g, 50.00 mmol) in ethanol (50 ml) was added hydrazine monohydrate (4.85 ml, 100 mmol) and the reaction mixture was heated at 70 ° C. for 5 h. The reaction mixture was cooled to room temperature and water (100 nml) was added. After 5 d, the reaction mixture was concentrated in vacuo to ca. 100 ml and diethyl ether (100 ml) was added. The layers were separated and the aqueous layer was extracted with diethyl ether (100 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo to afford ca. 8.0 g of a crude yellow oil. This was purified by chromatography in two batches Iusing a Biotage Flash 40M™ cartridge packed with silica gel (90 g) eluting with dichloromethane:diethyl ether (19:1) to afford the title compound as viscous yellow oil (4.20 g, 45%).

1. temperatureThe reaction mixture was cooled to room temperature
2. concentrationthe reaction mixture was concentrated in vacuo to ca. 100 ml and diethyl ether (100 ml)
3. additionwas added
4. customThe layers were separated
5. extractionthe aqueous layer was extracted with diethyl ether (100 ml)
6. dry with materialThe combined extracts were dried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customto afford ca. 8.0 g of a crude yellow oil
9. customThis was purified by chromatography in two batches
10. washeluting with dichloromethane:diethyl ether (19:1)

ORD record

ord-a55fbbdfaae443bb8d4741aa4a2849bc

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313312B1