Reaction #1973930

Reaction equation

N-(2-hydroxy-1-p-tolyl-propyl)-3-methylbezamide

phosphorus (V) oxide

decahydronaphtalene

→

1-(3-methylphenyl)-4,7-dimethylisoquinoline

Conditions

Workup

1. 1
   OtherAfter completion of the reaction
2. 2
   Extractionthe reaction mixture was extracted with dichloromethane and water
3. 3
   workup.DISTILLATIONdistilled under reduced pressure
4. 4
   OtherThe resulting residue was purified by silica gel column chromatography
5. 5
   workup.DISTILLATIONThe eluate was distilled under reduced pressure
6. 6
   OtherThe residue was recrystallized from dichloromethane and petroleum ether
7. 7
   Filtrationfiltered

Procedure

N-(2-hydroxy-1-p-tolyl-propyl)-3-methylbezamide (2.1 mmol), phosphorus (V) oxide (10 mmol) and decahydronaphtalene (50 mmol) were put in a dried two-neck round-bottom flask. Then, the mixture was stirred at 120 for 5 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane and water and distilled under reduced pressure. The resulting residue was purified by silica gel column chromatography. The eluate was distilled under reduced pressure. The residue was recrystallized from dichloromethane and petroleum ether, and filtered to yield 1-(3-methylphenyl)-4,7-dimethylisoquinoline.

Source