Reacción #60090

Ecuación de reacción

2-chloro-5-cyanopyridine

ethylene diamine

→

6-[(2-aminoethyl)amino]pyridine-3-carbonitrile

Rendimiento 78.0%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe ethylene diamine was removed under reduced pressure
2. 2
   Otrodried in vacuo for 2-3 h
3. 3
   Extracciónextracted with a solution of 95% ethyl acetate and 5% methanol (3×150 ml) and with a solution of 95% acetonitrile and 5% methanol (3×150 ml)
4. 4
   Extracciónextracted with a saturated sodium chloride solution (2×70 ml)
5. 5
   SecadoThe organic layer was dried with sodium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   OtroThe crude white to tan solid was triturated with ether (2×50 ml)
9. 9
   Otrodried overnight in vacuo

Procedimiento

A mixture of 2-chloro-5-cyanopyridine (0.60 M) in acetonitrile (120 ml) and ethylene diamine (85 ml) were stirred overnight (ca. 16 h) at 75-80° C. under argon. The ethylene diamine was removed under reduced pressure and then dried in vacuo for 2-3 h. The residual solution was basified with 1 M sodium hydroxide solution (˜100 ml). The aqueous solution was saturated with sodium chloride and extracted with a solution of 95% ethyl acetate and 5% methanol (3×150 ml) and with a solution of 95% acetonitrile and 5% methanol (3×150 ml). The organic extracts were combined and extracted with a saturated sodium chloride solution (2×70 ml). The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure. The crude white to tan solid was triturated with ether (2×50 ml) and dried overnight in vacuo resulting in 78% yield of 6-[(2-aminoethyl)amino]pyridine-3-carbonitrile.

Fuente