Hydrazinecarboxaldehyde → 3-(4-nitrophenyl)-1H-1,2,4-triazole
Reaction equation
Cl.CO[C:4](=[NH:14])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[CH:15]([NH:17][NH2:18])=O>N1C=CC=CC=1>[N+:11]([C:8]1[CH:7]=[CH:6][C:5]([C:4]2[NH:18][N:17]=[CH:15][N:14]=2)=[CH:10][CH:9]=1)([O-:13])=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
4-Nitro-benzimidic acid methyl ester hydrochloride (635 mg, 2.93 mmol) was suspended in pyridine (7 mL) and formic hydrazide (Aldrich, 178 mg, 2.95 mmol) was added and the mixture was stirred at rt for 1 hr. The solvent was removed and the residue was dissolved in toluene (10 mL) and the mixture was stirred at reflux for 1.5 hrs. the mixture was cooled and water was added. The organic layer was separated and dried over sodium sulfate. The solvent was removed and the residue was suspended in 25% EtOAc/Hexanes and the solid was filtered to give a solid. 510 mg.