Anthranilic Acid → Methyl Anthranilate

HRID 2175697Notes

Reaction equation

HRID 2175697 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O=S(Cl)Cl.[CH3:15]O>>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:15])=[O:5]

Participants

4

Reactant 3

HCID 227Anthranilic AcidHCID 887MethanolHCID 24386Thionyl Chloride

Product 1

HCID 8635Methyl AnthranilateYield 93%

Procedure

To a stirred solution of 2-aminobenzoic acid (2.0 g, 14.59 mmol) in MeOH (70 mL) at 0° C. was added SOCl2 (7.4 g, 145.9 mmol) dropwise. The mixture was heated at reflux overnight and was then concentrated under reduced pressure. DCM and saturated aqueous NaHCO3 were added and the aqueous phase extracted with DCM. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to afford methyl 2-aminobenzoate (2.05 g, 93%). LC-MS (ES-API); rt 8.46 min; m/z calculated for C8H9NO2[M+H]+ 152.0, found 152.1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationwas then concentrated under reduced pressure
  4. additionDCM and saturated aqueous NaHCO3 were added
  5. extractionthe aqueous phase extracted with DCM
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bfe36a928a2d4dd7af237d28467351d5
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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