Potassium Carbonate → 4-Methyl-2-phenylquinoline

HRID 2308153Notes

Reaction equation

HRID 2308153 reaction equation
Cl[C:2]1[CH:11]=[C:10]([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.COCCOC>[C:13]1([C:2]2[CH:11]=[C:10]([CH3:12])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 694492-Chloro-4-methylquinoline

Product 1

HCID 209194-Methyl-2-phenylquinolineYield 61%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-4-methylquinoline (5.0 g, 30 mmol) and phenyl boronic acid (4.4 g, 36 mmol) were dissolved into 100 mL of ethylene glycol dimethyl ether. To the stirred reaction was added triphenylphosphine (0.8 g) and palladium(II) acetate, followed by 50 mL of a 2 M solution of potassium carbonate. The reaction was refluxed for 16 hours. After cooling, the aqueous layer was discarded and additional ethyl acetate added. The organics were washed with a saturated solution of sodium chloride and separated. The organic layer was dried over magnesium sulfate, concentrated, and purified on a silica gel column using 20% ethyl acetate and hexanes as the eluants. The pure fractions were combined and concentrated to give 2-phenyl-4-methylquinoline (4.0 g, 61% yield) as an oil.

Workup

  1. customTo the stirred reaction
  2. temperatureThe reaction was refluxed for 16 hours
  3. temperatureAfter cooling
  4. washThe organics were washed with a saturated solution of sodium chloride
  5. customseparated
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated
  8. custompurified on a silica gel column
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e2cf8114536042a0951a2f81f871b771
Source dataset
uspto-grants-2004_12
Patent number
US06835469B2

Reaction notes

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