Reaktion #63201

Reaktionsgleichung

Sodium nitrite

3-amino-2-[3-(5,6,7,8-tetrahydroquinol-8-yl)propylamino]-5-(pyrid-3-ylmethyl)pyridine

sodium hydroxide

→

oil

Ausbeute 106.7%

3-(5,6,7,8-Tetrahydroquinol-8-yl)propyl-6-(pyrid-3-ylmethyl)-3H-1,2,3-triazolo[5,4-b]pyridine

Ausbeute 106.7%

Lösungsmittel

water

sulphuric acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred at 4° C. for 50 minutes
2. 2
   Temperaturto warm to room temperature
3. 3
   Extraktionextracted with chloroform (3×150 ml)
4. 4
   Trocknendried over magnesium sulphate
5. 5
   Sonstigethe solvent removed

Vorschrift

Sodium nitrite (1.3 g) in water (60 ml) was added over 25 minutes to a solution of 3-amino-2-[3-(5,6,7,8-tetrahydroquinol-8-yl)propylamino]-5-(pyrid-3-ylmethyl)pyridine (5.5 g) in molar sulphuric acid (250 ml) stirred at 4° C. The reaction mixture was stirred at 4° C. for 50 minutes, then allowed to warm to room temperature, basified with 10 molar sodium hydroxide solution to pH 13 and extracted with chloroform (3×150 ml). The chloroform extracts were combined, dried over magnesium sulphate, and the solvent removed to give a brown oil (6.04 g). The oil was chromatographed on silica in 5% MeOH/chloroform to give the title compound as an oil (3.61 g).

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