Reacción #6452

Ecuación de reacción

tin dichloride dihydrate

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

ethanol

→

3-Amino-4-(4'-cyanophenyl)aminopyridine

Disolventes

hydrochloric acid

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe resulting mixture was heated
2. 2
   Temperaturato reflux for 10 minutes under nitrogen
3. 3
   TemperaturaThe mixture was cooled in ice
4. 4
   Filtraciónfiltered
5. 5
   LavadoThe creamy-coloured solid was washed with 2N aqueous sodium hydroxide and water
6. 6
   Otrodried in a vacuum desiccator

Procedimiento

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 hydrochloric 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.

Fuente