4-Aminobenzonitrile → 4-[N-(4-Cyanophenyl)amino]-3-nitropyridine
Reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1Cl)([O-:3])=[O:2].[NH2:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.[NH4+].[OH-]>C(O)C>[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[NH:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)([O-:3])=[O:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution under N2 of 3-nitro-4-chloropyridine (4.63 g, 29.2 mmol), prepared as described by Wright, G. C., J. Heterocyclic Chem. 1976, 13, 601, and Kruger, S. and Mann, F. G., J. Chem. Soc. 2 1955, 758, in absolute ethanol (100 mL) was added 4-aminobenzonitrile (3.45 g, 29.2 mmol) and the resulting purple-brown solution was stirred for 17 hours at ambient temperature, during which time it became a green-brown suspension. The reaction mixture was poured into cold 10% aqueous NH4OH and filtered. The solid was suspended in ethanol (75 mL) and heated for 10 min on the steam bath. The suspension was cooled to ambient temperature and filtered to give 4-(N-3-nitropyrid-4-ylamino)benzonitrile as a bright-yellow solid.