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

HRID 249252Notes

Reaction equation

HRID 249252 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-cyanoaniIine (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 The solid
  2. additionwas treated with 150 ml of boiling ethanol
  3. temperaturecooled in ice
  4. filtrationfiltered

Sources & evidence

ORD record
ord-fec2c19bafbe4be784d973030e0a4074
Source dataset
uspto-grants-1993_05
Patent number
US05214044

Reaction notes

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