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

HRID 896736

Reaktionsgleichung

Reaktionsgleichung von HRID 896736
[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) was added dropwise at 100° C. to a solution of 3.50 g of o-bromoquinoline (16.8 mmol) in 50 ml of THF, and the mixture was stirred for 15 minutes at 80° C. Next, a solution of 50 ml of THF and 2.45 g of 2- methyl-1-indanone (16.8 mmol) was added within ten minutes to the lithiated bromoquinoline. The solution was left to return to room temperature, and subsequently boiled for three hours in reflux. After cooling to room temperature, ice was added and the mixture was acidified to pH 1 with hydrochloric acid, and subsequently heated under relfux for three hours. The reaction mixture was adjusted with ammonia solution to pH 9, and the aqueous phase was extracted with diethyl ether. The combined organic phases were dried, and the solvent was removed. The raw product was purified by distillation in a vacuum at 150 to 160° C. and 10−2 mbar. 1.5 g of 1-(8-quinolyl)-2-methylindene (45%) were obtained in the form of a viscous yellow resin.

Aufarbeitung

  1. waitThe solution was left
  2. customto return to room temperature
  3. waitsubsequently boiled for three hours
  4. temperaturein reflux
  5. temperatureAfter cooling to room temperature
  6. additionice was added
  7. temperaturesubsequently heated under relfux for three hours
  8. extractionthe aqueous phase was extracted with diethyl ether
  9. customThe combined organic phases were dried
  10. customthe solvent was removed
  11. distillationThe raw product was purified by distillation in a vacuum at 150 to 160° C.

Quellen und Nachweise

ORD-Eintrag
ord-f9422e90423f495bbd3a461ef7b1750d
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919412B1

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