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Sodium Carbonate → 2-(2-Methylphenyl)quinoline

HRID 2308148
Notes
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Reaction equation

HRID 2308148 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.[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

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

Product 1

HCID 6128242-(2-Methylphenyl)quinolineYield 88.3%

Reagents, catalysts & solvents 4

HCID 167845
palladium(II) acetate
Catalyst
HCID 962WaterSolvent
HCID 80711,2-DimethoxyethaneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f06b7e8b9d3a4448a7b93a75fe057ec0
Source dataset
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06835469B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes