Réaction #40269

Équation de réaction

4-(4-Aminophenyl)butyric acid

methanol

hydrogen chloride

→

methyl 4-(4-aminophenyl)butyrate hydrogen chloride

Conditions de réaction

Traitement

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

Mode opératoire

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