Reaktion #320977

Reaktionsgleichung

(4R)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole-6-carboxylic hydrazide

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title compound

Ausbeute 163.9%

(-)(4R)-6-(5-phenyl-1,3,4-oxadiazol-2-yl)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole

Ausbeute 163.9%

Lösungsmittel

trimethylorthobenzoate

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Extraktionthe product was extracted into aqueous tartaric acid
3. 3
   Extraktionthe product was extracted into methylene chloride
4. 4
   SonstigeEvaporation of the methylene chloride
5. 5
   workup.WAITleft crystalline product which
6. 6
   Sonstigewas then chromatographed over 3 g of silica gel
7. 7
   SonstigeThe product from the column was recrystallized from toluene

Vorschrift

A solution of 0.20 g (0.64 mmol) of (4R)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole-6-carboxylic hydrazide in 2.0 ml of trimethylorthobenzoate was heated at 135° C. under nitrogen for 5 hours. After cooling, the semisolid mixture was dissolved in methylene chloride and the product was extracted into aqueous tartaric acid. The aqueous solution was basified with sodium carbonate and the product was extracted into methylene chloride. Evaporation of the methylene chloride left crystalline product which was then chromatographed over 3 g of silica gel using ethyl acetate as eluent. The product from the column was recrystallized from toluene to give 0.21 g of title compound.

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