Sodium Carbonate → 2-Methyl-6-phenylquinoline

HRID 1892991Notes

Reaction equation

HRID 1892991 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[CH:6]=[CH:5]2.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCCO)C.C(OC(O)C)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:12][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:3]=2)[N:8]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic Acid2×HCID 5228856-Bromo-2-methylquinoline2×

Product 1

HCID 132664442-Methyl-6-phenylquinoline

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst2×HCID 962WaterSolventHCID 8076Glycol monoethyl etherSolvent2×HCID 101298981-EthoxyethanolSolvent

Procedure

2-Methyl-6-phenylquinoline was prepared from 6-Bromo-2-methylquinoline by Suzuki coupling with phenylboronic acid and tetrakis(triphenylphosphine) palladium(0) in refluxing 2-ethoxyethanol. To a solution 6-Bromo-2-methylquinoline (8.9 g; 40 mmol) in 2-ethoxyethanol (100 ml) was added tetrakis(triphenylphosphine) palladium (1 g; 0.86 mmol) and the reaction mixture was stirred at room temperature for 10 minutes. Phenylboronic acid (5 g; 41 mmol) in ethoxyethanol (50 ml) was then added followed by aqueous sodium carbonate (8.4 g; 79 mmol) in water (50 ml). The reaction mixture was magnetically stirred and refluxed for 16 h. The cooled reaction mixture was extracted with chloroform (3×100 ml), washed with brine, dried over anhydrous magnesium sulphate and solvent concentrated. The residue with the solvent was filtered through a silica gel column and the colourless solution was evaporated. The residue was triturated with petroleum spirit (30-40° C.) and recrystallised from ether to give an off white solid, 5.5 g (63%); Mp 95° C. (DSC, onset). Elemental analysis: Found C, 87.60; H, 5.98; N, 6.32; C16H13N requires C, 87.64; H, 5.98; and N, 6.39%.

Workup

  1. stirringThe reaction mixture was magnetically stirred
  2. temperaturerefluxed for 16 h
  3. customThe cooled reaction mixture
  4. extractionwas extracted with chloroform (3×100 ml)
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulphate and solvent
  7. concentrationconcentrated
  8. filtrationThe residue with the solvent was filtered through a silica gel column
  9. customthe colourless solution was evaporated
  10. customThe residue was triturated with petroleum spirit (30-40° C.)
  11. customrecrystallised from ether
  12. customto give an off white solid, 5.5 g (63%)

Sources & evidence

ORD record
ord-ba1dea94e7df4480bd0060f1b0785fa9
Source dataset
uspto-grants-2013_08
Patent number
US08507896B2

Reaction notes

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