Methanol → Methyl 5-amino-2-hydroxybenzoate

HRID 1776578Notes

Reaction equation

HRID 1776578 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH3:17]O>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:17])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 40755-Aminosalicylic Acid

Product 1

HCID 135127Methyl 5-amino-2-hydroxybenzoateYield 89%

Procedure

5-Amino-2-hydroxybenzoic acid (10 g, 65.3 mmol) was suspended in MeOH (150 ml), and aqueous 96% sulfuric acid (12 ml, 225 mmol) was added drop wise. The mixture was heated to reflux for 96 hours. After cooling to RT, the solvent was partially removed under vacuum; the remaining solution was basified with NaHCO3 5% and extracted with EtOAc. The organic layer was washed with brine and dried over Na2SO4. The solvent was evaporated under vacuum affording methyl 5-amino-2-hydroxybenzoate as a solid (9.68 g, 57.9 mmol, 89% yield, MS/EST+168.0 [MH]+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 96 hours
  3. customthe solvent was partially removed under vacuum
  4. extractionextracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-573856824ba34aceb1278250bad5d6be
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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