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

HRID 1088662Notes

Reaction equation

HRID 1088662 reaction equation
[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)#[N:2].Cl[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18]>C(O)C>[C:1]([C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 133964-AminobenzonitrileHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 105620064-[N-(4-Cyanophenyl)amino]-3-nitropyridineYield 86.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to the method of J. C. S. Perkin Trans. I, 1979, 135, p-cyanoaniline (6.894 g, 58.4 mmol) was added to a solution of 4-chloro-3-nitropyridine (9.26 g, 58.4 mmol) in ethanol (200 ml) and the mixture was stirred at room temperature for 18 hours. The resulting yellow suspension was poured into 500 ml of ice-cold dilute ammonia and filtered. The solid was treated with 150 ml of boiling ethanol, cooled in ice, and filtered to give the title compound as a bright yellow powder, (12.15 g), m.p. 210°-211° C.

Workup

  1. filtrationfiltered
  2. additionThe solid was treated with 150 ml of boiling ethanol
  3. temperaturecooled in ice
  4. filtrationfiltered

Sources & evidence

ORD record
ord-64cd5925305940b99730126fac585964
Source dataset
uspto-grants-1990_10
Patent number
US04963560

Reaction notes

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