Reaction #40269

Reaction equation

4-(4-Aminophenyl)butyric acid

methanol

hydrogen chloride

→

methyl 4-(4-aminophenyl)butyrate hydrogen chloride

Conditions

Workup

1. 1
   Otherwas bubbled through the solution
2. 2
   TemperatureAfter the reaction mixture was cooled to room temperature
3. 3
   workup.ADDITIONethyl ether (100 ml.) was added
4. 4
   OtherThe mixture, which separated into two layers
5. 5
   FiltrationThe crystalline product was collected by filtration
6. 6
   Otherdried thoroughly
7. 7
   OtherThe filtrate was evaporated to dryness
8. 8
   Otherthe residue was recrystallized from MeOH/benzene

Procedure

4-(4-Aminophenyl)butyric acid (5 g) was dissolved in 40 ml methanol. The solution was refluxed at 80-90° C. with stirring for 4 h while hydrogen chloride gas was bubbled through the solution. After the reaction mixture was cooled to room temperature, ethyl ether (100 ml.) was added. The mixture, which separated into two layers, was refrigerated overnight. The crystalline product was collected by filtration and dried thoroughly. The filtrate was evaporated to dryness and the residue was recrystallized from MeOH/benzene. The total amount of the product methyl 4-(4-aminophenyl)butyrate hydrogen chloride obtained was 5.6 g (87.5%), m.p. 143-145° C.

Source