Potassium Carbonate → 3-Methyl-2-phenylquinoline

HRID 1795726Notes

Reaction equation

HRID 1795726 reaction equation
[CH3:1][C:2]1[C:3](Cl)=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[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+]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:13]1([C:3]2[C:2]([CH3:1])=[CH:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 3390822-Chloro-3-methylquinoline

Product 1

HCID 14820143-Methyl-2-phenylquinolineYield 99.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

3-methyl-2-chloroquinoline (29.71 g, 167 mmol), phenylboronic acid (24.4 g, 200 mmol), triphenylphosphine (4.388 g, 16.7 mmole) and 2M K2CO3 aqueous soln. (225 mL) were dissolved in the 264 mL of ethylene glycol dimethyl ether. To the stirred solution was added palladium acetate (0.94 g, 4.18 mmole) and the mixture was refluxed under N2 for 20 hours. The reaction mixture was cooled and the water was extracted with methylene chloride three times. The combined organic phase was washed with portions of brine. The organic layer was then dried with anhydrous sodium sulfate, filtered, and evaporated of solvent. The crude material was purified by kegelrohr distillation to give 1 (36.31 g, 98.6%).

Workup

  1. temperaturethe mixture was refluxed under N2 for 20 hours
  2. temperatureThe reaction mixture was cooled
  3. extractionthe water was extracted with methylene chloride three times
  4. washThe combined organic phase was washed with portions of brine
  5. dry with materialThe organic layer was then dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated of solvent
  8. distillationThe crude material was purified by kegelrohr distillation

Sources & evidence

ORD record
ord-389081a1e3d041468d35fc36a8e5b837
Source dataset
uspto-grants-2006_04
Patent number
US07029765B2

Reaction notes

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