1,2-Dibromoethane → 1-(2-Bromoethyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-one

HRID 276897

Reaktionsgleichung

Reaktionsgleichung von HRID 276897
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[CH2:10][CH2:11][CH2:12][CH:3]([C:4]=23)[C:2]1=[O:13].[H-].[Na+].[Br:16][CH2:17][CH2:18]Br>CN(C)C=O>[Br:16][CH2:17][CH2:18][N:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[CH2:10][CH2:11][CH2:12][CH:3]([C:4]=23)[C:2]1=[O:13]

Komponenten

5

Edukt 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 5993752a,3,4,5-Tetrahydrobenzo[cd]indol-2(1H)-one

Produkt 1

HCID 226295731-(2-Bromoethyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-oneAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2a,3,4,5-Tetrahydrobenz[cd]indole-2(1H) -one (3.46 g, 20mmol) was dissolved in anhydrous N,N-dimethylformamide (20 ml). Thereto was added sodium hydride (0.8 g, 20 mmol), and the resulting solution was stirred at room temperature for 1 hour. The reaction solution was mixed with 1,2-dibromoethane (10 ml, 115 mmol) and again stirred for 1 hour. The reaction solution was extracted by adding 100 ml of ethyl acetate and 100 ml of water, and the resulting ethyl acetate layer was separated, washed with water and dried with anhydrous sodium sulfate. Then the compound obtained by the evaporation of the solvent under a reduced pressure was crystallized from a dimethylformamide-water mixture to obtain 1.9 g of the title compound (34% in yield).

Aufarbeitung

  1. stirringagain stirred for 1 hour
  2. extractionThe reaction solution was extracted
  3. additionby adding 100 ml of ethyl acetate and 100 ml of water
  4. customthe resulting ethyl acetate layer was separated
  5. washwashed with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThen the compound obtained by the evaporation of the solvent under a reduced pressure
  8. customwas crystallized from a dimethylformamide-water mixture

Quellen und Nachweise

ORD-Eintrag
ord-161e0de06b4448e39e039f9cdf33adef
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355642B1

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