(2-Nitrophenyl)hydrazine → 5-Cyclopropyl-2,4-dihydro-2-(2-nitrophenyl)-3H-1,2,4-triazol-3-one

HRID 36231

Reaction equation

HRID 36231 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]1

Participants

4

Reactant 2

HCID 3314739(2-Nitrophenyl)hydrazineHCID 54370041HCID 54370041, compound

Product 1

HCID 1357200845-Cyclopropyl-2,4-dihydro-2-(2-nitrophenyl)-3H-1,2,4-triazol-3-oneYield 69%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

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)+.

Sources & evidence

ORD record
ord-bba17d0917914d9fb6f8e3e9787e2847
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

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