Reaction #11950

Reaction equation

8-Aminoquinoline

potassium carbonate

methyl 4-bromomethylbenzoate

→

title compound

Yield 172.4%

Methyl 4-(8-quinolylaminomethyl)benzoate

Yield 172.4%

Solvents

DMF

Conditions

Workup

1. 1
   Concentrationthe reaction solution was concentrated
2. 2
   workup.ADDITIONThe resulting residue was diluted with chloroform and water
3. 3
   workup.ADDITIONwas added
4. 4
   ExtractionThe mixture was extracted with chloroform
5. 5
   WashThe organic layer was washed with saturated brine
6. 6
   Dryingdried over anhydrous sodium sulfate
7. 7
   Concentrationconcentrated

Procedure

8-Aminoquinoline (1.26 g) was dissolved in DMF (20 ml), and potassium carbonate (1.2 g) and methyl 4-bromomethylbenzoate (1.0 g) were added. After stirring for 20 hours, the reaction solution was concentrated. The resulting residue was diluted with chloroform and water was added. The mixture was extracted with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to obtain the title compound (2.20 g) as a yellow syrup.

Source