1,2-Dimethoxyethane → HCID 1481967, compound

HRID 2308151Notes

Reaction equation

HRID 2308151 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][C:17](B(O)O)=[CH:16][CH:15]=1.COCCOC>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].O>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 119282-ChloroquinolineHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 1481967HCID 1481967, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Procedure

2-Chloroquinoline (5.0 g, 31 mmol) and 4-methoxyphenylboronic acid (5.5 g, 36 mmol) were dissolved in a solvent mixture containing 40 mL ethylene glycol dimethyl ether and 60 mL water containing 12.0 g K2CO3. To the stirred solution was added 1.6 g tetrakis(triphenylphosphine)palladium(O) and the mixture refluxed under N2 overnight. The cooled reaction mixture was then removed of water, extracted with methylene chloride three times. The combined organic phase was washed with portions of brine and then dried with anhydrous sodium sulfate, filtered, and evaporated of solvent to give 2-(p-methoxyphenyl)quinoline (5.0 g) after column chromatography (20% ethyl acetate in hexane).

Workup

  1. temperaturethe mixture refluxed under N2 overnight
  2. customThe cooled reaction mixture
  3. customwas then removed of water
  4. extractionextracted with methylene chloride three times
  5. washThe combined organic phase was washed with portions of brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated of solvent

Sources & evidence

ORD record
ord-c059d12fac2047e3a12aacfa1c35b3fa
Source dataset
uspto-grants-2004_12
Patent number
US06835469B2

Reaction notes

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