Ammonia → HCID 68506250, compound

HRID 1712883Notes

Reaction equation

HRID 1712883 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][CH:21]([CH3:24])[C:22]=1[CH3:23].Cl.N>O1CCCC1>[CH3:17][C:18]1[C:22]([CH3:23])=[C:21]([CH3:24])[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 343352,3,4-Trimethyl-2-cyclopenten-1-oneHCID 1401098-BromoquinolineHCID 178418339Butyllithium

Product 1

HCID 68506250HCID 68506250, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-80 °C

Procedure

A solution of 8.3 g (40 mmol) of 8-bromoquinoline in 100 ml of tetrahydrofuran was cooled to −80° C. and 16 ml of n-butyllithium (2.5 M in hexane, 40 mmol) were subsequently added dropwise. After the addition was complete, the mixture was stirred for a further 15 minutes at −80° C. and 4.96 g (40 mmol) of 2,3,4-trimethylcyclopent-2-enone were then added. The mixture was allowed to come to room temperature and was then refluxed for 30 minutes. After cooling to room temperature, the reaction mixture was admixed with ice water and 10 ml of concentrated hydrochloric acid and stirred for 30 minutes. A dilute aqueous ammonia solution was then 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. Distillation at 117-132° C. and 2×10−2 mbar gave 4.02 g (17.1 mmol, 43%) of 2,3,4-trimethyl-1-(8-quinolyl)cyclopentadiene.

Workup

  1. additionAfter the addition
  2. customto come to room temperature
  3. temperaturewas then refluxed for 30 minutes
  4. temperatureAfter cooling to room temperature
  5. stirringstirred for 30 minutes
  6. customThe aqueous phase was then separated off from the organic phase
  7. extractionthe aqueous phase was extracted twice with diethyl ether
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. distillationthe solvent was distilled off
  11. distillationDistillation at 117-132° C.

Sources & evidence

ORD record
ord-ee9ffb0d02cc4de2af5efef34a14d7af
Source dataset
uspto-grants-2010_09
Patent number
US07795167B2

Reaction notes

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