Hydrochloric Acid → 1-(8-Quinolyl)-indan-1-ol

HRID 2304941Notes

Reaction equation

HRID 2304941 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:26])[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[C:17]2([OH:26])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:19][CH2:18]2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

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

Product 1

HCID 223521191-(8-Quinolyl)-indan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-100 °C

Procedure

8-Bromoquinoline (10.4 g, 50 mmol) was introduced into 100 ml of THF, and the mixture was cooled to about −100° C. 20 ml of n-BuLi (2.5 M in hexane, 50 mmol) were added dropwise, during which the internal temperature was kept below −80° C. When the addition was complete, the mixture was stirred at −80° C. for a further 15 minutes, and 6.6 g of 1-indanone (50 mmol), dissolved in 30 ml of THF, were then added dropwise. The reaction mixture was then allowed to warm slowly to room temperature, and was then refluxed for 3 hours. After the mixture had cooled to room temperature, firstly ice and then hydrochloric acid were added to about pH 1, and the mixture was stirred for 30 minutes. The aqueous and organic phases were separated, the aqueous phase was treated with ammonia solution to about pH 9 and extracted with ether, and the combined organic phases were subsequently evaporated to dryness under reduced pressure. The viscous oil obtained in this way (1-(8-quinolyl)-indan-1-ol (8H2O)) was treated with hydrochloric acid to pH 0, refluxed for 2 hours and subsequently neutralized. After work-up and drying, 6.6 g of 1-(8-quinolyl)indene (55%) were isolated as a colorless solid.

Workup

  1. customwas kept below −80° C
  2. additionWhen the addition
  3. additionwere then added dropwise
  4. temperatureto warm slowly to room temperature
  5. temperaturewas then refluxed for 3 hours
  6. temperatureAfter the mixture had cooled to room temperature
  7. stirringthe mixture was stirred for 30 minutes
  8. customThe aqueous and organic phases were separated
  9. additionthe aqueous phase was treated with ammonia solution to about pH 9
  10. extractionextracted with ether
  11. customthe combined organic phases were subsequently evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-2885e83055ae4e3db88f1861ff8db7f7
Source dataset
uspto-grants-2002_08
Patent number
US06437161B1

Reaction notes

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