Reacción #1596994

Ecuación de reacción

5-aminosalicylic acid

triethylamine

benzyl bromide

→

5-benzylaminosalylic acid

Rendimiento 113.8%

5-benzylaminosalicylic acid

Rendimiento 113.8%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONIce chips were added to the reaction mixture
2. 2
   Otrosolvent was removed in vacuo
3. 3
   workup.ADDITIONThe reaction mixture was diluted with water
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   LavadoThe organic layer was washed with water and brine
6. 6
   Secadodried over anhydrous MgSO4
7. 7
   OtroAfter evaporation of the solvent
8. 8
   Otrothe residue was purified by column chromatography
9. 9
   Otrorecrystallized from methanol/ethyl acetate/hexane (1:3:1)

Procedimiento

To a solution of 5-aminosalicylic acid (2.0 g, 13 mmole, purchased from Aldrich Chemical Company, USA) and triethylamine in dried DMF (25 ml) was added benzyl bromide (2.68 g, 1.90 ml, 15.6 mmole) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred for 4 hr at room temperature. Ice chips were added to the reaction mixture and then solvent was removed in vacuo. The reaction mixture was diluted with water and then extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous MgSO4. After evaporation of the solvent, the residue was purified by column chromatography and recrystallized from methanol/ethyl acetate/hexane (1:3:1) to give 3.6 g (73% yield) of 5-benzylaminosalylic acid as a white solid.:mp 173.5-174.5° C. (decompose).

Fuente