Ammonia → 1-(8-Quinolyl)-2-methylindene

HRID 1005643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1005643
[Li]CCCC.[CH3:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]1=O.Br[C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1.Cl.N>C1COCC1>[N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][C:21]=2[CH:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:15]=[C:7]2[CH3:6])[CH:26]=[CH:27][CH:18]=1

Komponenten

7

Edukt 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 2492622-MethylindanoneHCID 27627562-BromoquinolineHCID 178418339Butyllithium

Produkt 1

HCID 219779771-(8-Quinolyl)-2-methylindeneAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

6.70 ml of n-BuLi (16.8 mmol) were added dropwise at 100° C. to 3.50 g of o-bromoquinoline (16.8 mmol) dissolved in 50 ml of THF, and the mixture was subsequently stirred at 80° C. for 15 minutes. A solution of 50 ml of THF and 2.45 g of 2-methyl-1-indanone (16.8 mmol) was then added to the lithiated bromoquinoline over the course of 10 minutes. The mixture was allowed to cool to room temperature, and the solution was then refluxed for three hours, cooled to room temperature, acidified to pH 1 using ice and hydrochloric acid and subsequently refluxed for three hours. The reaction mixture was adjusted to pH 9 using ammonia solution, and the aqueous phase was extracted with diethyl ether. The combined organic phases were dried, and the solvent was removed. The crude product was purified by distillation under reduced pressure at 150-160° C./10−2 mbar, giving 1.5 g of 1-(8-quinolyl)-2-methylindene (45%) as a yellow, viscous resin.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. temperaturethe solution was then refluxed for three hours
  3. temperaturecooled to room temperature
  4. temperaturesubsequently refluxed for three hours
  5. extractionthe aqueous phase was extracted with diethyl ether
  6. customThe combined organic phases were dried
  7. customthe solvent was removed
  8. distillationThe crude product was purified by distillation under reduced pressure at 150-160° C./10−2 mbar

Quellen und Nachweise

ORD-Eintrag
ord-f4b34a6256b6471b9743b9db0fd5b253
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787498B2

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