Sulfuric Acid → Methyl p-aminosalicylate

HRID 1969155Notes

Reaction equation

HRID 1969155 reaction equation
NC1C=C(O)C(=CC=1)C(O)=O.S(=O)(=O)(O)O.S(=O)(=O)(O)O.[NH2:22][C:23]1[CH:24]=[C:25]([OH:33])[C:26](=[CH:31][CH:32]=1)[C:27]([O:29][CH3:30])=[O:28]>CO>[NH2:22][C:23]1[CH:24]=[C:25]([OH:33])[C:26](=[CH:31][CH:32]=1)[C:27]([O:29][CH3:30])=[O:28]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 46494-Aminosalicylic AcidHCID 68720411Methyl 4-aminosalicylate bisulfate

Product 1

HCID 77787Methyl p-aminosalicylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Aminosalicylic acid (12.3 g) is placed in a round bottom flask. The flask is charged with 150 mL of methanol and 20 mL of concentrated sulfuric acid. The reaction mixture is brought to gentle reflux for 1 day, and then allowed to cool to room temperature. The mixture is further chilled in a freezer and methyl 4-aminosalicylate bisulfate is crystallized. The crystals are collected and washed with cold methanol to afford 15.8 g of the product as off-white needles.

Workup

  1. temperatureto gentle reflux for 1 day
  2. customis crystallized
  3. customThe crystals are collected
  4. washwashed with cold methanol

Sources & evidence

ORD record
ord-bb920c2585ae4fb0a0001d7bd4a424b0
Source dataset
uspto-grants-2013_04
Patent number
US08426466B2

Reaction notes

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