Toluene → 1-Phenylisoquinoline

HRID 1820567Notes

Reaction equation

HRID 1820567 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][N:12]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[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.C(O)C>[C:1]1([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 140539Isoquinoline, 1-chloro-

Product 1

HCID 1378821-PhenylisoquinolineYield 43%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Procedure

3.04 g of phenylboronic acid (24.9 mmol) and 4.09 g of 1-chloroisoquinoline (25.0 mmol), 25 ml of toluene, 12.5 ml of ethanol, and 25 ml of a 2M sodium carbonate aqueous solution were introduced into a 100 ml-three-neck flask. With stirring at room temperature under a nitrogen gas flow, 0.98 g (0.85 mmol) of tetrakis-(triphenylphosphine) palladium (0) was added to the mixture. Thereafter, the resultant was stirred under reflux under a nitrogen gas flow for 8 hours. After completion of the reaction, the reaction product was cooled, and then extracted with cool water and toluene. The organic layer was washed with saline and dried with magnesium sulfate, and then the solvent was dried under reduced pressure. The residue was purified using silica gel column chromatography (eluent: chloroform/methanol: 10/1), to yield 2.20 g of 1-phenylisoquinoline (43.0% yield).

Workup

  1. additionwas added to the mixture
  2. temperatureunder reflux under a nitrogen gas flow for 8 hours
  3. customAfter completion of the reaction
  4. temperaturethe reaction product was cooled
  5. extractionextracted with cool water and toluene
  6. washThe organic layer was washed with saline
  7. dry with materialdried with magnesium sulfate
  8. customthe solvent was dried under reduced pressure
  9. customThe residue was purified

Sources & evidence

ORD record
ord-0bbe044330294415bc8718de82208907
Source dataset
uspto-grants-2009_10
Patent number
US07604683B2

Reaction notes

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