Réaction #577216

Équation de réaction

sodium carbonate

phenylboronic acid

1-chloroisoquinoline

toluene

→

1-phenylisoquinoline

Rendement 43.0%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   TempératureThereafter, reflux
3. 3
   AutreAfter completion of the reaction
4. 4
   Températurethe reaction product was cooled
5. 5
   Extractionextracted by addition of cold water and toluene
6. 6
   LavageThe organic layer was washed with saline water
7. 7
   Autredried on magnesium sulfate
8. 8
   Autrefollowed by removal of the solvent under a reduced pressure
9. 9
   Autreto provide
10. 10
    Autredry solid
11. 11
    AutreThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol 10/1)

Mode opératoire

In a 100 ml-three-necked flask, 3.04 g (24.9 mmole) of phenylboronic acid (made by Tokyo Kasei), 4.0 g of (25.0 mmole) of 1-chloroisoquinoline, 25 ml of toluene, 12.5 ml of ethanol and 25 ml 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 was 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 2.20 g (yield=43.0%) of 1-phenylisoquinoline. FIG. 7 shows a 1H-NMR spectrum of a solution of the compound in heavy chloroform.

Source