Hydrazine hydrate (1:1) → 3,3,3-Trifluoro-1-(3-nitrophenyl)-1-propanone hydrazone
Reaction equation
[F:1][C:2]([F:16])([F:15])[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1)=O.O.[NH2:18][NH2:19]>O1CCCC1>[F:1][C:2]([F:16])([F:15])[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1)=[N:18][NH2:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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%).