Methanol → Methyl 5-amino-2-hydroxybenzoate

HRID 2251702Notes

Reaction equation

HRID 2251702 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.[CH3:12]O>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:12])=[O:8]

Participants

3

Reactant 2

HCID 887MethanolHCID 40755-Aminosalicylic Acid

Product 1

HCID 135127Methyl 5-amino-2-hydroxybenzoateYield 76%

Procedure

To a solution of 5-aminosalicylic acid (3.00 g, 19.6 mmole) in methanol (80 ml) was added c-H2SO4 (8 ml) at 0° C. After the reaction mixture was refluxed for 6 hr, the solvent was removed in vacuo. The resulting residue was partitioned with ethyl acetate and water. The organic layer was washed with water (40 ml×3) and then dried over anhydrous MgSO4. After evaporation of the solvent, the residue was recrystallized from ethyl acetate/hexane to give 2.50 g (76% yield) of methyl 5-amino-2-hydroxybenzoate as a yellow solid.

Workup

  1. temperatureAfter the reaction mixture was refluxed for 6 hr
  2. customthe solvent was removed in vacuo
  3. customThe resulting residue was partitioned with ethyl acetate and water
  4. washThe organic layer was washed with water (40 ml×3)
  5. dry with materialdried over anhydrous MgSO4
  6. customAfter evaporation of the solvent
  7. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-6c03e88958df4bfcbac5e46879076db4
Source dataset
uspto-grants-2008_01
Patent number
US07319160B2

Reaction notes

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