HCID 53980652, Verbindung → 2-(Pyridin-3-yl)propan-1-amine
Reaktionsgleichung
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([CH3:12])[CH2:8][N+:9]([O-])=O)[CH:2]=1>C(O)C.Cl.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([CH3:12])[CH2:8][NH2:9])[CH:2]=1Komponenten
5
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
To a solution of 2-(3-pyridyl)-1-nitropropane (0.91 g, 5.48 mmol) in 20 mL of ethanol and 0.1 mL of 12N HCl was added 10% Pd/C (1.00 g) under argon. The solution was evacuated and flushed with hydrogen several times, place under an atmosphere of hydrogen and vigorously stirred. After 14 h the mixture was evacuated and flushed with argon several times, filtered through celite and washed with 200 mL of ethanol. The volatiles were removed in vacuo to provide a residue which was partitioned between methylene chloride (100 mL) and NaOH (50 mL, 10%) and the aqueous layer was extracted with methylene chloride (2×100 mL). The combined organic layers were dried over MgSO4, filtered, concentrated in vacuo and the residue was purified by flash column chromatography (20×150 mm column of SiO2, CH2Cl2 /CH2Cl2 saturated with NH3 /MeOH 60:39:1) to give the title compound as an oil: