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

HRID 2175719Notes

Reaction equation

HRID 2175719 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].O=S(Cl)Cl.[CH3:16]O>>[NH2:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Participants

4

Reactant 3

HCID 863-Hydroxyanthranilic AcidHCID 887MethanolHCID 24386Thionyl Chloride

Product 1

HCID 205248Anthranilic acid, 3-hydroxy-, methyl esterYield 95%

Procedure

To a stirred solution of 2-amino-3-hydroxybenzoic acid (1.22 g, 8.0 mmol) in MeOH (80 mL) was added SOCl2 (9.52 g, 80.0 mmol) dropwise at 0° C. The mixture was then heated at reflux overnight. Most of the methanol was removed and the residue was partitioned between DCM and saturated aqueous NaHCO3. The organic phase was washed with brine, dried over sodium sulfate and the solvent was removed under reduced pressure to give methyl 2-amino-3-hydroxybenzoate (1.27 g, 95%). LC-MS (ES-API); rt 8.09 min; m/z calculated for C8H9NO3 [M+H]+ 168.1, found 168.1.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux overnight
  3. customMost of the methanol was removed
  4. customthe residue was partitioned between DCM and saturated aqueous NaHCO3
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4be67d80b57c4bcd972ee407d9378a24
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

Loading…