Ammonia → HCID 68423784, compound

HRID 1984991Notes

Reaction equation

HRID 1984991 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[O:23][Si](C)(C)C.Cl.N>O1CCCC1>[CH3:17][C:18]1[C:22](=[O:23])[CH2:21][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 1401098-BromoquinolineHCID 3364292-methyl-3-(trimethylsilyloxy)cyclopent-2-enoneHCID 178418339Butyllithium

Product 1

HCID 68423784HCID 68423784, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-80 °C

Procedure

A mixture of 38.7 g (186 mmol) of 8-bromoquinoline and 250 ml of tetrahydrofuran was cooled to −80° C., and 74.4 ml of n-butyllithium (2.5 M in hexane, 186 mmol) were subsequently added while stirring. The mixture was stirred for a further 15 minutes and 49.9 g (186 mmol) of 2-methyl-3-(trimethylsilyloxy)cyclopent-2-enone were added while stirring. The mixture was allowed to warm to room temperature while stirring and stirring was continued for a further one hour. The reaction mixture was then hydrolyzed by means of a mixture of 40 g of ice and 30 ml of concentrated hydrochloric acid and the mixture obtained in this way was refluxed for 3 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 obtained in this way was distilled at 119-139° C. and 2×10−2 mbar to give 31.1 g (139.3 mmol, 74.9%) of 2-methyl-3-(8-quinolyl)cyclopent-2-enone.

Workup

  1. stirringThe mixture was stirred for a further 15 minutes
  2. stirringwhile stirring
  3. temperatureto warm to room temperature
  4. stirringwhile stirring
  5. stirringstirring
  6. customthe mixture obtained in this way
  7. temperaturewas refluxed for 3 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. customThe residue obtained in this way
  16. distillationwas distilled at 119-139° C.

Sources & evidence

ORD record
ord-58ef407979c14d0cbd4575912d5db1fe
Source dataset
uspto-grants-2009_06
Patent number
US07544826B2

Reaction notes

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