Potassium Carbonate → Methyl 6-(4-methylphenyl)-2-methylquinoline-3-carboxylate

HRID 1387961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1387961
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:5]2.B([O-])([O-])O[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(CCO)=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:25][C:22]1[CH:23]=[CH:24][C:19]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([CH3:12])[C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:5]3)=[CH:20][CH:21]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 18472460Methyl 6-bromo-2-methylquinoline-3-carboxylateHCID 866453334-Methylphenyl borate

Produkt 1

HCID 18472437Methyl 6-(4-methylphenyl)-2-methylquinoline-3-carboxylateAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 66602552Toluene-ethanol waterLösungsmittel

Versuchsvorschrift

Under argon atmosphere, a solution of methyl 6-bromo-2-methylquinoline-3-carboxylate (1.22 g), 4-methylphenyl borate (0.65 g) and potassium carbonate (1.18 g) in toluene-ethanol-water (40-4-4 ml) was stirred at room temperature for 1 hour. To the reaction mixture was added tetrakistriphenylphosphinepalladium (0.15 g), and the mixture was refluxed for 18 hours and cooled to room temperature. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:1) to give methyl 6-(4-methylphenyl)-2-methylquinoline-3-carboxylate (1.27 g) as colorless crystals.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 18 hours
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate/hexane=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-29318a8f4ddc4bd08e2bd431eb9edeee
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06268354B1

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