Réaction #6452

Équation de réaction

tin dichloride dihydrate

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

ethanol

→

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

Solvants

hydrochloric acid

water

Conditions de réaction

Traitement

1. 1
   Températurethe resulting mixture was heated
2. 2
   Températureto reflux for 10 minutes under nitrogen
3. 3
   TempératureThe mixture was cooled in ice
4. 4
   Filtrationfiltered
5. 5
   LavageThe creamy-coloured solid was washed with 2N aqueous sodium hydroxide and water
6. 6
   Autredried in a vacuum desiccator

Mode opératoire

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.

Source