Ethanol → 3-Amino-4-[N-(4-cyanophenyl)amino]pyridine

HRID 1886171Notes

Reaction equation

HRID 1886171 reaction equation
O.O.[Sn](Cl)Cl.[C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2C=C[C:17]([NH2:20])=[C:16]([N+:21]([O-])=O)[CH2:15]2)=[CH:10][CH:9]=1)#[N:7].[CH2:24](O)[CH3:25]>O>[NH2:21][C:16]1[CH:17]=[N:20][CH:24]=[CH:25][C:15]=1[NH:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]#[N:7])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 61436Stannous chloride dihydrateHCID 19791284N-(4-cyanophenyl)-4-amino-3-nitropyridine

Product 1

HCID 105364203-Amino-4-[N-(4-cyanophenyl)amino]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

According to a modification of the method of Pharm. Helv. Acta, 1975, 50, 188., tin dichloride dihydrate (56.4 g, 250 mmol) was added to a suspension of N-(4-cyanophenyl)-4-amino-3-nitropyridine (12.0 g, 50 mmol) in 2N aqueous hydrocholoric acid (35 ml), water (150 ml) and ethanol (75 ml) and the resulting mixture was heated to reflux for 10 minutes under nitrogen. The mixture was cooled in ice, poured into ice-cold 2N aqueous sodium hydroxide (400 ml) and filtered. The creamy-coloured solid was washed with 2N aqueous sodium hydroxide and water, and then dried in a vacuum desiccator. The product, 3-amino-4-(4'-cyanophenyl)aminopyridine, 9.31 g, gradually turns reddish brown on exposure to light and air.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 10 minutes under nitrogen
  3. temperatureThe mixture was cooled in ice
  4. filtrationfiltered
  5. washThe creamy-coloured solid was washed with 2N aqueous sodium hydroxide and water
  6. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-ab71e08a831341e2a77d75d65b3f2cc0
Source dataset
uspto-grants-1992_09
Patent number
US05149814

Reaction notes

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