Anthranilic Acid → Benzoic acid, 2-amino-, 1-methylethyl ester

HRID 1294561Notes

Reaction equation

HRID 1294561 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].S(Cl)(Cl)=O.[CH3:15][CH:16](O)[CH3:17]>>[NH2:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH:16]([CH3:17])[CH3:15])=[O:9]

Participants

4

Reactant 3

HCID 227Anthranilic AcidHCID 3776IsopropanolHCID 24386Thionyl Chloride2×

Product 1

HCID 87499Benzoic acid, 2-amino-, 1-methylethyl ester

Procedure

1.0 g (7.3 mmol) anthranilic acid are dissolved in 5 ml propan-2-ol, combined with 795 μl (10.9 mmol) thionyl chloride and refluxed for 3 days. Then thionyl chloride is eliminated in vacuo, the residue is taken up in 50 ml dist. water and extracted three times with 30 ml of ethyl acetate. The organic phase is washed with 20 ml of a saturated aqueous NaHCO3 solution, dried with MgSO4 and the solvent is eliminated in vacuo.

Workup

  1. temperaturerefluxed for 3 days
  2. extractionwater and extracted three times with 30 ml of ethyl acetate
  3. washThe organic phase is washed with 20 ml of a saturated aqueous NaHCO3 solution
  4. dry with materialdried with MgSO4

Sources & evidence

ORD record
ord-ebc38455508b4e25a78d9749207a0db0
Source dataset
uspto-grants-2007_07
Patent number
US07241769B2

Reaction notes

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