Ammonia → HCID 68956838, compound

HRID 1984994Notes

Reaction equation

HRID 1984994 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.C([Li])CCC.[CH3:17][C:18]1[C:19](=O)[CH2:20][CH2:21][C:22]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].Cl.N>O1CCCC1>[CH3:17][C:18]1[C:22]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:21][CH2:20][C:19]=1[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 798172-Cyclopenten-1-one, 2-methyl-3-pentyl-HCID 1401098-BromoquinolineHCID 178418339Butyllithium

Product 1

HCID 68956838HCID 68956838, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.8 g (32 mmol) of 8-bromoquinoline in 90 ml of tetrahydrofuran was cooled to −90° C., and 12.8 ml of n-butyllithium (2.5 M in hexane, 32 mmol) were subsequently added while stirring. After stirring for 15 minutes at this temperature, 5.3 g (32 mmol) of 2-methyl-3-pentylcyclopent-2-enone (dihydroisojasmone) were added while stirring. The mixture was stirred at this temperature for a further one hour, allowed to warm to room temperature and then refluxed for one hour. After cooling to room temperature, a mixture of 30 g of ice and 30 g of concentrated hydrochloric acid was added and the resulting mixture was refluxed for 2 hours. The mixture was allowed to cool to room temperature while stirring and ammonia solution was added until a pH of 12 had been reached. The aqueous phase was then separated off from the organic phase and the aqueous phase was extracted twice with diethyl ether. The organic phases were combined, dried over magnesium sulfate, filtered and the solvent was distilled off. The residue was dissolved in 5 ml of toluene and then admixed with 80 ml of hexane. The precipitate formed was filtered off and dried. The residue obtained in this way was distilled at >110° C. and 1×10−2 mbar to give 2.6 g of 2-methyl-3-pentyl-1-(8-quinolyl)cyclopentadiene.

Workup

  1. additionwere added
  2. stirringwhile stirring
  3. stirringThe mixture was stirred at this temperature for a further one hour
  4. temperaturerefluxed for one hour
  5. temperatureAfter cooling to room temperature
  6. additionwas added
  7. temperaturethe resulting mixture was refluxed for 2 hours
  8. temperatureto cool to room temperature
  9. stirringwhile stirring
  10. customThe aqueous phase was then separated off from the organic phase
  11. extractionthe aqueous phase was extracted twice with diethyl ether
  12. dry with materialdried over magnesium sulfate
  13. filtrationfiltered
  14. distillationthe solvent was distilled off
  15. dissolutionThe residue was dissolved in 5 ml of toluene
  16. customThe precipitate formed
  17. filtrationwas filtered off
  18. customdried
  19. customThe residue obtained in this way
  20. distillationwas distilled at >110° C.

Sources & evidence

ORD record
ord-f63fa61d9c4e43ec8617b2d6945116d9
Source dataset
uspto-grants-2009_06
Patent number
US07544826B2

Reaction notes

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