Reaction #577218

Reaction equation

sodium carbonate

4-methylphenyl-boronic acid

1-chloroisoquinoline

toluene

→

1-(4-methylphenyl)isoquinoline

Yield 51.1%

Solvents

ethanol

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   TemperatureThereafter, reflux
3. 3
   OtherAfter completion of the reaction
4. 4
   Temperaturethe reaction product was cooled
5. 5
   Extractionextracted by addition of cold water and toluene
6. 6
   WashThe organic layer washed with saline water
7. 7
   Otherdried on magnesium sulfate
8. 8
   Otherfollowed by removal of the solvent under a reduced pressure
9. 9
   Otherto provide
10. 10
    Otherdry solid The residue
11. 11
    Otherwas purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

Procedure

In a 200 ml-three-necked flask, 3.40 g (25.0 mmole) of 4-methylphenyl-boronic acid (made by Aldrich Co.), 4.09 g (25.0 mmole) of 1-chloroisoquinoline, 25 ml of toluene, 12.5 ml of ethanol and 25 mol of 2M-sodium carbonate aqueous solution were placed and stirred at room temperature under nitrogen stream, and 0.98 g (0.85 mmole) of tetrakis(triphenylphosphine)-palladium (0) was added thereto. Thereafter, reflux under stirring was performed for 8 hours under nitrogen stream. After completion of the reaction, the reaction product was cooled and extracted by addition of cold water and toluene. The organic layer washed with saline water and dried on magnesium sulfate, followed by removal of the solvent under a reduced pressure to provide dry solid The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1) to obtain 2.80 g (yield=51.1%) of 1-(4-methylphenyl)isoquinoline.

Source