Hydrazine hydrate (1:1) → 3,3,3-Trifluoro-1-(3-nitrophenyl)-1-propanone hydrazone

3,3,3-Trifluoro-1-(3-nitrophenyl)-1-propanone (Sov. Prog. Chem. (Engl.Transi.), 1966, 32, 745, 1.8 g, 7.72 mmol) was dissolved in tetrahydrofuran (10 ml) and hydrazine monohydrate (0.56 ml, 11.58 mmol) was added dropwise at room temperature. The reaction mixture was stirred for 1 h at room temperature then heated under reflux for 40 min. The reaction mixture was concentrated in vacui and the residue treated with water (10 ml) and extracted with dichloromethane (4×10 ml). The organic extracts were concentrated in vacuo and the residue was purified by chromatography on silica gel (100 g), eluting with diciforomethane: hexane (1:1 and then 2:1). The product was obtained as an amber gum (159 mg, 8%).

1. temperaturethen heated
2. temperatureunder reflux for 40 min
3. concentrationThe reaction mixture was concentrated in vacui
4. additionthe residue treated with water (10 ml)
5. extractionextracted with dichloromethane (4×10 ml)
6. concentrationThe organic extracts were concentrated in vacuo
7. customthe residue was purified by chromatography on silica gel (100 g)
8. washeluting with diciforomethane

ORD record

ord-c53229ee727247eaacefae25216cfb7a

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313312B1