Reaktion #2508176

Reaktionsgleichung

hydrazine monohydrate

hydrogen chloride-ethyl acetate

phthalimide

triphenylphosphine

DEAD toluene

4-(2-Hydroxyethyl)pyridine-2-carbonitrile

4-(2-hydroxyethyl)pyridine-2-carbonitrile

→

4-(2-aminoethyl)pyridine-2-carbonitrile dihydrochloride

Ausbeute 55.0%

Lösungsmittel

Ethanol

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthe reaction mixture was concentrated under reduced pressure
2. 2
   workup.ADDITIONDiethyl ether was added to the residue
3. 3
   Filtrationthe resulting precipitate was collected by filtration
4. 4
   workup.STIRRINGthe mixture was stirred at 70° C. for 2 hours
5. 5
   FiltrationAfter the resulting precipitate was collected by filtration
6. 6
   Einengenthe filtrate was concentrated under reduced pressure
7. 7
   Filtrationa further precipitate was collected by filtration
8. 8
   Sonstigeprecipitated crystals
9. 9
   Filtrationwere collected by filtration

Vorschrift

4-(2-Hydroxyethyl)pyridine-2-carbonitrile (2.53 g, 17.1 mmol) obtained in Step 4 was dissolved in THF (40.0 mL), then phthalimide (3.02 g, 20.5 mmol), triphenylphosphine (5.38 g, 20.5 mmol), and a DEAD-toluene solution (40.0%, 8.93 g, 20.5 mmol) were added thereto, followed by stirring at room temperature for 1 hour. After completion of the reaction was confirmed by thin-layer chromatography, the reaction mixture was concentrated under reduced pressure. Diethyl ether was added to the residue, and the resulting precipitate was collected by filtration. Ethanol (200 mL) and hydrazine monohydrate (2.57 g, 51.3 mmol) were added to the resulting solid, and the mixture was stirred at 70° C. for 2 hours. After the resulting precipitate was collected by filtration, the filtrate was concentrated under reduced pressure, and a further precipitate was collected by filtration. A hydrogen chloride-ethyl acetate solution (4.00 mol/L, 50.0 mL, 200 mmol) was added to the filtrate, and precipitated crystals were collected by filtration to give 4-(2-aminoethyl)pyridine-2-carbonitrile dihydrochloride (2.05 g, yield 55%).

Quelle