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

HRID 1655250Notes

Reaction equation

HRID 1655250 reaction equation
[CH:1]1[C:6]([C:7]#[N:8])=[CH:5][CH:4]=[C:3]([NH2:9])[CH:2]=1.Cl[C:11]1C=C[N:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].[CH2:20](O)[CH3:21]>>[C:7]([C:6]1[CH:5]=[CH:4][C:3]([N:9]2[CH:21]=[CH:20][C:13]([NH2:14])=[C:12]([N+:17]([O-:19])=[O:18])[CH2:11]2)=[CH:2][CH:1]=1)#[N:8]

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-9e795bb4c2e046ff92e974c5ef20aa72
Source dataset
uspto-grants-1993_10
Patent number
US05250531

Reaction notes

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