4-Aminobenzonitrile → 4-[N-(4-Cyanophenyl)amino]-3-nitropyridine

HRID 375629Notes

Reaction equation

HRID 375629 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

HCID 133964-AminobenzonitrileHCID 14923Ammonium HydroxideHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 105620064-[N-(4-Cyanophenyl)amino]-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. filtrationfiltered
  2. temperatureheated for 10 min on the steam bath
  3. temperatureThe suspension was cooled to ambient temperature
  4. filtrationfiltered

Sources & evidence

ORD record
ord-34108c11cb3b414a80cbcc09cac1baa3
Source dataset
uspto-grants-1996_01
Patent number
US05486525

Reaction notes

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