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.Transl.), 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 vacuo 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 dichloromethane: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 vacuo
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 dichloromethane:hexane (1:1

ORD record

ord-db3cadd7c75d498d8cb29467a307ce85

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07049444B2