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

HRID 380520

Reaction equation

HRID 380520 reaction equation
[NH2:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[CH3:13]O>>[CH3:13][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([OH:11])[C:2]=1[NH2:1]

Participants

4

Reactant 3

HCID 863-Hydroxyanthranilic AcidHCID 313Hydrochloric AcidHCID 887Methanol

Product 1

HCID 205248Anthranilic acid, 3-hydroxy-, methyl ester

Procedure

To a solution of 2 g (13.1 mmol) of 2-amino-3-hydroxybenzoic acid in 60 mL of CH3OH at 0° C. was bubbled HCl gas until the solution was saturated. The reaction was heated at reflux for 12 h. The reaction mixture was concentrated and dissolved in 30 mL of water. The solution was neutralized with sat'd NaHCO3 solution and extracted with EtOAc. The organic fractions were dried over MgSO4, filtered and the filtrate was concentrated to give 1.8 g of the title compound as a brown solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 12 h
  3. concentrationThe reaction mixture was concentrated
  4. dissolutiondissolved in 30 mL of water
  5. extractionextracted with EtOAc
  6. dry with materialThe organic fractions were dried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-705586a0a1d6491bae150b800fb4e115
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Linked notes

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