Ethanol → N-(4-cyanophenyl)-4-amino-3-nitropyridine

HRID 892759

Reaction equation

HRID 892759 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]1C=C[N:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].[CH2:20](O)[CH3:21]>>[C:1]([C:3]1[CH:9]=[CH:8][C:6]([N:7]2[CH:21]=[CH:20][C:13]([NH2:14])=[C:12]([N+:17]([O-:19])=[O:18])[CH2:11]2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 133964-AminobenzonitrileHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 19791284N-(4-cyanophenyl)-4-amino-3-nitropyridine

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 N-(4-cyanophenyl)-4-amino-3-nitropyridine, 12.15 g, as a bright yellow powder, 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-311d6e67ac3c48c49b38f8bacf7171dc
Source dataset
uspto-grants-1992_06
Patent number
US05120747

Linked notes

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