Reacción #336435

Ecuación de reacción

tin(II) dichloride dihydrate

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

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

→

title compound

Rendimiento 88.6%

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

Rendimiento 88.6%

Disolventes

hydrochloric acid

water

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe resulting mixture was heated
2. 2
   Temperaturaunder reflux for 10 minutes under nitrogen
3. 3
   TemperaturaThe mixture was cooled in ice
4. 4
   Filtraciónfiltered The creamy-coloured solid
5. 5
   Lavadowas 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, 50, 188 (1975), tin(II) dichloride dihydrate (56.4 g, 250 mmol) was added to a suspension of 4-[N-(4-cyanophenyl)amino]-3-nitropyridine (see part (a)) (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 under 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 to provide the title compound, (9.31 g), which gradually turns reddish brown on exposure to light and air.

Fuente