Ethylene Glycol → HCID 21476735, Verbindung

HRID 260291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 260291
C([N:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:18](=O)[CH2:19][CH2:20][CH:11]([C:12]=23)[CH2:10]1)(=O)C1C=CC=CC=1.[OH-].[K+].O.NN.C(O)CO>O>[NH:9]1[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[CH2:18][CH2:19][CH2:20][CH:11]([C:12]=23)[CH2:10]1

Komponenten

6

Edukt 4

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 570263HCID 570263, Verbindung

Produkt 1

HCID 21476735HCID 21476735, VerbindungAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 5.0 g of 1-benzoyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-one, 2.7 g of potassium hydroxide, 2 ml of hydrazine hydrate and 20 ml of ethylene glycol was heated at 120° C. for 2 hours and then at 190° C. for 3 hours. After mixture cooling, water was added, and the reaction product was extracted with dichloromethane. After the extract was dried over magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: dichloromethane-ethyl acetate=10:1 (v/v)) to yield 1.9 g of 1,2,2a,3,4,5-hexahydrobenz[cd]indole as a colorless crystal having a melting point of 58° to 59° C.

Aufarbeitung

  1. temperatureAfter mixture cooling
  2. extractionthe reaction product was extracted with dichloromethane
  3. dry with materialAfter the extract was dried over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (developing solvent: dichloromethane-ethyl acetate=10:1 (v/v))

Quellen und Nachweise

ORD-Eintrag
ord-b0bca5d8be6740e3be04b78bf8efea38
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05527800

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