Reaction #1596994

Reaction equation

5-aminosalicylic acid

triethylamine

benzyl bromide

→

5-benzylaminosalylic acid

Yield 113.8%

5-benzylaminosalicylic acid

Yield 113.8%

Solvents

DMF

Conditions

Workup

1. 1
   workup.ADDITIONIce chips were added to the reaction mixture
2. 2
   Othersolvent was removed in vacuo
3. 3
   workup.ADDITIONThe reaction mixture was diluted with water
4. 4
   Extractionextracted with ethyl acetate
5. 5
   WashThe organic layer was washed with water and brine
6. 6
   Dryingdried over anhydrous MgSO4
7. 7
   OtherAfter evaporation of the solvent
8. 8
   Otherthe residue was purified by column chromatography
9. 9
   Otherrecrystallized from methanol/ethyl acetate/hexane (1:3:1)

Procedure

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).

Source