تفاعل #577216

معادلة التفاعل

sodium carbonate

phenylboronic acid

1-chloroisoquinoline

toluene

→

1-phenylisoquinoline

المردود 43.0%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   درجة الحرارةThereafter, reflux
3. 3
   أخرىAfter completion of the reaction
4. 4
   درجة الحرارةthe reaction product was cooled
5. 5
   استخلاصextracted by addition of cold water and toluene
6. 6
   غسيلThe organic layer was washed with saline water
7. 7
   أخرىdried on magnesium sulfate
8. 8
   أخرىfollowed by removal of the solvent under a reduced pressure
9. 9
   أخرىto provide
10. 10
    أخرىdry solid
11. 11
    أخرىThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol 10/1)

الإجراء التجريبي

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.

المصدر