تفاعل #554595

ord-d586ef9163c8494087d4dc094c93c9cb

معادلة التفاعل

CC(C)(C)N=Cc1ccccc1I
tert-butyl-(2-iodo-benzylidene)amine
CC(C)c1ccccc1
Propane-2-yl-benzene
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
CN(C)C=O
DMF
Cc1cc(C)cc(-c2ncc3ccccc3c2C)c1
3-(3,5-dimethylphenyl)-4-methylisoquinoline

ظروف التفاعل

درجة الحرارة
100°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىAfter completion of the reaction
  2. 2
    درجة الحرارةto cool to room temperature
  3. 3
    استخلاصThe reaction mixture was extracted with ether and saturated NH4Cl
  4. 4
    workup.DISTILLATIONThe extract was distilled under reduced pressure
  5. 5
    أخرىThe resulting residue was purified by silica gel column chromatography (hexane: EtOAc=5:1)

الإجراء التجريبي

Propane-2-yl-benzene (100 mmol), acetic acid palladium (2.7 mmol), triphenylphosphine (5 mmol), and sodium carbonate (50 mmol) were put in a dried two-neck round-bottom flask and dissolved in DMF (100 ml). Subsequently, tert-butyl-(2-iodo-benzylidene)amine (50 mmol) was added thereto. The resulting solution was stirred in a bath at 100° C. for 24 hours. After completion of the reaction, the temperature was allowed to cool to room temperature. The reaction mixture was extracted with ether and saturated NH4Cl. The extract was distilled under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane: EtOAc=5:1) to yield 3-(3,5-dimethylphenyl)-4-methylisoquinoline.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08623519B2uspto-grants-2014_01