Potassium Carbonate → 2-(2-Methoxyphenyl)quinoline

HRID 2308149Notes

Reaction equation

HRID 2308149 reaction equation
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.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=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

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 119282-ChloroquinolineHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 125036672-(2-Methoxyphenyl)quinoline

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Chloroquinoline (2.45 g, 15.0 mmol), o-methoxyphenylboronic acid (2.73 g, 18.0 mmol,) and potassium carbonate (5.59 g, 40.4 mmol) were dissolved in 40 mL ethylene glycol dimethyl ether and 20 mL of water. To the stirred solution was added tetrakis(triphenylphosphine)palladium(O) (1.04 g, 0.89 mmol) and the entire mixture was allowed to reflux under a N2 atmosphere for 20 hours. The cooled reaction mixture was then removed of water. Additional ethyl acetate (150 mL) was added and the solvent was washed three times using 100 mL portions of brine. The organic layer was dried with anhydrous sodium sulfate, filtered, and the solvent concentrated. The residue purified via column chromatography using 50% ethyl acetate/hexanes as the eluents to give 2-(o-methoxyphenyl)quinoline.

Workup

  1. temperatureto reflux under a N2 atmosphere for 20 hours
  2. customThe cooled reaction mixture
  3. customwas then removed of water
  4. additionAdditional ethyl acetate (150 mL) was added
  5. washthe solvent was washed three times
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe solvent concentrated
  9. customThe residue purified via column chromatography

Sources & evidence

ORD record
ord-15d8034cd7f74a8db0999cc100c02fd1
Source dataset
uspto-grants-2004_12
Patent number
US06835469B2

Reaction notes

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