Benzonitrile → HCID 53389671, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:17])/[CH:4]=[C:5](\[NH:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)/[CH3:6].[C:18](#[N:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:1][O:2][C:3]([C:4]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:25][N:7]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[C:5]=1[CH3:6])=[O:17]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
According to AVV A, (Z-3-(4-nitrophenylamino)-but-2-enoic acid methylester (236.2 mg, 1.0 mmol, 1.0 equiv.) was stirred with Cu(OAc)2 (544.9 mg, 3.0 mmol, 3.0 equiv.) into benzonitrile (3.0 ml, 29.4 mmol, 29.4 equiv.) for 14 hours at 120° C. The brown solid obtained as raw product (533.2 mg) was purified by means of column chromatography (silica gel (50 g), CH2Cl2/EtOAc 100:0→90:10→0:100), whereby the pure product was obtained in the form of a slightly yellowish solid (253.5 mg, 0.75 mmol, 75%).