3-Hydroxyanthranilic Acid → Anthranilic acid, 3-hydroxy-, methyl ester

HRID 583302Notes

Reaction equation

HRID 583302 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH2:11].[C:12](=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:12][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([OH:1])[C:3]=1[NH2:11]

Participants

4

Reactant 2

HCID 863-Hydroxyanthranilic AcidHCID 10340Sodium Carbonate

Product 1

HCID 205248Anthranilic acid, 3-hydroxy-, methyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.0 g (6.53 mmol) of 3-hydroxyanthranilic acid in 15 mL of methanol was added 5.0 mL of BF3 -methanol complex and the resulting solution was heated to reflux for 24 h. After cooling to room temperatue the reaction mixture was poured into saturated sodium carbonate solution and then extracted with ether. The combined organics were washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo to provide 0.90 g (83%) of the desired product as a brown solid. Electrospray Mass Spec: 167.8 (M+H)+

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for 24 h
  3. temperatureAfter cooling to room temperatue the reaction mixture
  4. extractionextracted with ether
  5. washThe combined organics were washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-275ec99cc56349a4b7d0da37594f460a
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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