Ammonia → 1-(8-Quinolyl)-2,3-dimethylcyclopentadiene

HRID 47833Notes

Reaction equation

HRID 47833 reaction equation
[Li]CCCC.Br[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2.[CH3:17][C:18]1[C:19](=O)[CH2:20][CH2:21][C:22]=1[CH3:23].Cl.N>C1COCC1>[N:15]1[C:16]2[C:11](=[CH:10][CH:9]=[CH:8][C:7]=2[C:19]2[CH2:20][CH:21]=[C:22]([CH3:23])[C:18]=2[CH3:17])[CH:12]=[CH:13][CH:14]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 142702-Cyclopenten-1-one, 2,3-dimethyl-HCID 1401098-BromoquinolineHCID 178418339Butyllithium

Product 1

HCID 223521241-(8-Quinolyl)-2,3-dimethylcyclopentadieneYield 41.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5 ml of n-BuLi (2.5 M in hexane, 12.5 mmol) were added dropwise at −95° C. to a solution of 2.5 g of 8-bromoquinoline (12 mmol) in 120 ml of THF, the mixture was stirred for 15 minutes, and 1.3 g of 2,3-dimethylcyclopent-2-enone (12 mmol) dissolved in 10 ml of THF were subsequently added. After warming to room temperature, the solution was refluxed for one hour. The cooled reaction mixture was hydrolyzed using ice, acidified using hydrochloric acid and then neutralized using ammonia solution. The aqueous phase was extracted with diethyl ether, and the combined organic phases were dried. Distillation at 150° C./0.05 mbar gave 1.1 g of 1-(8-quinolyl)-2,3-dimethylcyclopentadiene (40%) as a yellow, viscous oil.

Workup

  1. additionwere subsequently added
  2. temperaturethe solution was refluxed for one hour
  3. customThe cooled reaction mixture
  4. extractionThe aqueous phase was extracted with diethyl ether
  5. customthe combined organic phases were dried
  6. distillationDistillation at 150° C./0.05 mbar

Sources & evidence

ORD record
ord-f017544e06f04fcd845165beadfa3de0
Source dataset
uspto-grants-2004_03
Patent number
US06699948B2

Reaction notes

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