Ethylenediamine → 2,6-Diamino-N2-(2-aminoethyl)-5-nitropyridine

Temperature

77.5 °C

A mixture of 2-amino-6-chloro-3-nitropyridine (0.52 M) in acetonitrile (70 ml), and ethylene diamine (40 ml) were stirred overnight (ca. 20 h) at 75-80° C. under argon. The ethylene diamine was removed under reduced pressure. The residual solution was basified with 1M sodium hydroxide solution (50 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 (2×75 ml). The organic layer was dried with sodium sulfate, filtered, and concentrated under reduced pressure. The crude yellow solid was triturated with ether (2×25 ml) and dried overnight in vacuo resulting in 2-(2-aminoethyl)amino-6-amino-5-nitropyridine in 99% yield.

1. customThe ethylene diamine was removed under reduced pressure
2. extractionextracted 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)
3. extractionextracted with a saturated sodium chloride solution (2×75 ml)
4. dry with materialThe organic layer was dried with sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe crude yellow solid was triturated with ether (2×25 ml)
8. customdried overnight in vacuo
9. customresulting in 2-(2-aminoethyl)amino-6-amino-5-nitropyridine in 99% yield

ORD record

ord-9405b5e3bf8445c38ebfd73a4c558f98

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06489344B1