Anthranilic Acid → Ethyl 2-aminobenzoate

HRID 42036

Reaction equation

HRID 42036 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH2:16](O)[CH3:17]>>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:16][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 227Anthranilic AcidHCID 702EthanolHCID 1118Sulfuric Acid

Product 1

HCID 6877Ethyl 2-aminobenzoateYield 78%

Procedure

To a solution of 2-aminobenzoic acid (7.29 mmol, 1.0 g) in ethanol (20 ml), H2SO4 (45 mmol, 2.5 ml) was added and the mixture was refluxed for 20 hours. The solvent was evaporated and the crude residue was dissolved in water. The solution neutralised with 6N NaOH aqueous solution and extracted with CHCl3. The organic phase was evaporated affording 0.939 g (yield 78%) of the expected product.

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. customThe solvent was evaporated
  3. dissolutionthe crude residue was dissolved in water
  4. extractionextracted with CHCl3
  5. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-4b37735ad9534962a4502eed81159ae0
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Linked notes

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