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Sodium Carbonate → 2-(2-Methylphenyl)quinoline

HRID 2308148
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2308148
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:12]1([CH3:27])[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1C1C=CC=CC=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O.COCCOC>[CH3:27][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 119282-ChloroquinolineHCID 15887404(2'-Methyl-[1,1'-biphenyl]-2-yl)boronic acid

Produkt 1

HCID 6128242-(2-Methylphenyl)quinolineAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845
palladium(II) acetate
Katalysator
HCID 962WaterLösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a 500 mL round bottom flask was added, 2-chloroquinoline (4.7 g, 31 mmol), o-tolylphenyl boronic acid (4.7 g, 36 mmol) into 100 mL of ethylene glycol dimethyl ether. Sodium carbonate (8.9 g, 84 mmol) was dissolved into 50 mL of distilled water and added to the reaction mixture. After the addition of 0.1 mole % of triphenylphosphine (0.8 g) followed by 0.025 mol % of palladium(II) acetate (0.2 g). the reaction was heated under a nitrogen atmosphere for 4 hours. After cooling, additional ethyl acetate was added and the aqueous layer discarded. The organic layer was washed with a saturated solution of brine. The organic layer was dried over magnesium sulfate, filtered and the solvent removed by a rotary evaporator. The crude yellow oil was purified by column chromatography using a silica gel column and 20% ethyl acetate/hexanes as the eluants. The pure product was collected, combined and concentrated to give 2-(2-methylphenyl)quinoline (6.0 g, 75% yield).

Aufarbeitung

  1. additionTo a 500 mL round bottom flask was added
  2. additionadded to the reaction mixture
  3. temperaturethe reaction was heated under a nitrogen atmosphere for 4 hours
  4. temperatureAfter cooling
  5. washThe organic layer was washed with a saturated solution of brine
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent removed by a rotary evaporator
  9. customThe crude yellow oil was purified by column chromatography
  10. customThe pure product was collected
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f06b7e8b9d3a4448a7b93a75fe057ec0
Quelldatensatz
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06835469B2

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