Hydrochloric Acid → 1-(8-Quinolyl)indene

HRID 896734Notes

Reaction equation

HRID 896734 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 219779971-(8-Quinolyl)indeneYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-100 °C

Procedure

30 8-bromoquinoline (10.4 g, 50 mmol) was first placed in 100 ml of THF and cooled to approximately −100° C. 20 ml of n-BuLi (2.5 M in hexane, 50 mmol) were added dropwise, and the internal temperature was kept below −80° C. After the addition was ended, stirring was continued for a further 15 minutes at −80° C., and then 6.6 g of 1-indanone (50 mmol), dissolved in 30 ml of THF, were added dropwise. The reaction mixture was then allowed to return to room temperature slowly and then heated for three hours. in reflux. Once the mixture had cooled to room temperature, first ice and then hydrochloric acid was added to approximately pH 1, and the mixture was stirred for 30 minutes. The aqueous and organic phases were separated; the aqueous phase was mixed with ammonia solution to a pH of approximately 9 and extracted with ether, and the combined organic phases were then concentrated until dry in a vacuum. The thus-obtained viscous oil (1-(8-quinolyl)-indan-1-ol (8H2O)) was mixed with hydrochloric acid until the pH was 0, heated for two hours in reflux, and then neutralized. After processing and drying, 6.6 g of 1-(8-quinolyl)indene (55%) were obtained in the form of a colorless solid.

Workup

  1. customwas kept below −80° C
  2. additionAfter the addition
  3. additionwere added dropwise
  4. customto return to room temperature
  5. temperatureheated for three hours
  6. temperaturein reflux
  7. temperatureOnce the mixture had cooled to room temperature
  8. stirringthe mixture was stirred for 30 minutes
  9. customThe aqueous and organic phases were separated
  10. additionthe aqueous phase was mixed with ammonia solution to a pH of approximately 9
  11. extractionextracted with ether
  12. concentrationthe combined organic phases were then concentrated
  13. customuntil dry in a vacuum
  14. additionThe thus-obtained viscous oil (1-(8-quinolyl)-indan-1-ol (8H2O)) was mixed with hydrochloric acid until the pH was 0
  15. temperatureheated for two hours
  16. temperaturein reflux
  17. customdrying

Sources & evidence

ORD record
ord-31c669ae2c1e45799a531f824ac32784
Source dataset
uspto-grants-2005_07
Patent number
US06919412B1

Reaction notes

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