5-Aminosalicylic Acid → 5-benzylaminosalicylic acid

HRID 1509812Notes

Reaction equation

HRID 1509812 reaction equation
[NH2:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([NH:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 40755-Aminosalicylic AcidHCID 7498Benzyl BromideHCID 8471Triethylamine

Product 1

HCID 98995885-benzylaminosalicylic acidYield 113.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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).

Workup

  1. additionIce chips were added to the reaction mixture
  2. customsolvent was removed in vacuo
  3. additionThe reaction mixture was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous MgSO4
  7. customAfter evaporation of the solvent
  8. customthe residue was purified by column chromatography
  9. customrecrystallized from methanol/ethyl acetate/hexane (1:3:1)

Sources & evidence

ORD record
ord-6e00296bdf714b0ea2b06fa0d785057a
Source dataset
uspto-grants-2012_07
Patent number
US08211877B2

Reaction notes

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