Methanol → Methyl p-aminosalicylate

HRID 1421694Notes

Reaction equation

HRID 1421694 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[CH3:12]O>>[CH3:12][O:7][C:6](=[O:8])[C:5]1[C:4](=[CH:3][C:2]([NH2:1])=[CH:10][CH:9]=1)[OH:11]

Participants

3

Reactant 2

HCID 887MethanolHCID 46494-Aminosalicylic Acid

Product 1

HCID 77787Methyl p-aminosalicylate

Procedure

4-Aminosalicyclic acid (1 g, 98 mmol) was dissolved in MeOH. HCl(g) was bubbled through until the solution was saturated. The reaction mixture was heated at 70° for 16 hours. Additional MeOH was added to the reaction and saturated again with HCl (g). The reaction was heated at 70° for another 16 hours. The reaction mixture was neutralized with saturated NaHCO3 and extracted with EtOAc. The resulting solid was recrystallized from hot 2:1 hexane/EtOAc and collected on a frit. The solid was further purified by flash chromatography eluting the product with 2/1 hexane/EtOAc to give 4-aminosalicyclic acid methyl ester as a solid.

Workup

  1. customHCl(g) was bubbled through until the solution
  2. temperatureThe reaction mixture was heated at 70° for 16 hours
  3. additionAdditional MeOH was added to the reaction and saturated again with HCl (g)
  4. temperatureThe reaction was heated at 70° for another 16 hours
  5. extractionextracted with EtOAc
  6. customThe resulting solid was recrystallized from hot 2:1 hexane/EtOAc
  7. customcollected on a frit
  8. customThe solid was further purified by flash chromatography
  9. washeluting the product with 2/1 hexane/EtOAc

Sources & evidence

ORD record
ord-7698e48ee2914bfc921a3da49a92b6f2
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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