Hydrochloric Acid → 1-(8-Quinolyl)indene

HRID 1072698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072698
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Li]CCCC.[C:17]1(=O)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18]1.Cl>C1COCC1>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[CH:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)[CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 67351-IndanoneHCID 1401098-BromoquinolineHCID 178418339Butyllithium

Produkt 1

HCID 219779971-(8-Quinolyl)indeneAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

10.4 g (50 mmol) of 8-bromoquinoline in 100 ml of THF were cooled to about −100° C. 20 ml of n-BuLi (2.5M in hexane, 50 mmol) were added dropwise within a period of 5 min while the internal temperature was held below −80° C. After this addition stirring was continued at −80° C. for a further 15 min, and 6.6 g of 1-indanone (50 mmol) dissolved in 30 ml of THF were then added dropwise within a period of 10 min. The reaction mixture was then allowed to reach room temperature gradually and was then heated for 3 b at reflux. Once the mixture had cooled to room temperature, ice was added, followed by hydrochloric acid until the pH was about 1, followed by stirring for 30 min. The aqueous and organic phase were separated. The aqueous phase was mixed with ammonia solution until the pH was about 9 and extracted with ether. The combined organic phases were then evaporated to dryness in vacuo. The resultant viscous oil (1-(8-quinolyl)indan-1-ol (8H2O)) vas mixed with hydrochloric acid until the pH was 0, heated at reflux for 2 hours and then neutralised. After work-up and drying it was possible to isolate 6.6 g of 1-(8-quinolyl)indene (55%) as a colorless solid.

Aufarbeitung

  1. customwas held below −80° C
  2. additionAfter this addition
  3. additionwere then added dropwise within a period of 10 min
  4. customto reach room temperature
  5. temperaturewas then heated for 3 b
  6. temperatureat reflux
  7. additionice was added
  8. stirringby stirring for 30 min
  9. customThe aqueous and organic phase were separated
  10. additionThe aqueous phase was mixed with ammonia solution until the pH was about 9
  11. extractionextracted with ether
  12. customThe combined organic phases were then evaporated to dryness in vacuo
  13. additionThe resultant viscous oil (1-(8-quinolyl)indan-1-ol (8H2O)) vas mixed with hydrochloric acid until the pH was 0
  14. temperatureheated
  15. temperatureat reflux for 2 hours
  16. customAfter work-up and drying it

Quellen und Nachweise

ORD-Eintrag
ord-54c274ec3ebf49adbbfe9aec77d2b870
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911516B1

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