(2-Nitrophenyl)hydrazine → 5-Cyclopropyl-2,4-dihydro-2-(2-nitrophenyl)-3H-1,2,4-triazol-3-one
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][NH2:11])([O-:3])=[O:2].[C:12]([N:17]=[C:18]([CH:22]1[CH2:24][CH2:23]1)OCC)(OCC)=[O:13]>CO.C(Cl)Cl>[CH:22]1([C:18]2[NH:17][C:12](=[O:13])[N:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])[N:11]=2)[CH2:24][CH2:23]1Participants
4
Procedure
By the procedure of Example 4, Step C, 2-nitrophenylhydrazine was reacted with ethyl N-(carbethoxy)cyclopropanecarboximidate. After work-up, the residue was purified by flash chromatography on silica gel (150 mL for 2.0 mmole, eluted with 1.5% MeOH/CH2Cl2) to give the desired material as a yellow foam in 69% yield, homogeneous by TLC in 5% MeOH/CH2Cl2, mass spectrum (FAB) m/e 247 (M+1)+.