Ethanol → Ethyl 2-aminobenzoate

HRID 2163561Notes

Reaction equation

HRID 2163561 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[NH2:6].[CH2:12](O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:1]([O:2][C:3](=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[NH2:6])[CH3:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 8635Methyl AnthranilateHCID 11430Potassium Carbonate

Product 1

HCID 6877Ethyl 2-aminobenzoateYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

453 parts of anthranilic acid methyl ester are refluxed with 900 parts of ethanol and 30 parts of potassium carbonate for half an hour. Methanol which is set free during the reaction is then distilled off over a column. The complete transesterification requires about 20 hours. After an intermediate fraction containing methanol and ethanol as well, the excess of ethanol is distilled off. By distillation of the residue under reduced pressure there are obtained 441 parts of anthranilic acid ethyl ester (boiling point 113°-122° C. under 3-5 mm Hg, nD25 1,564; anthranilic acid methyl ester cannot be traced by gas chromatography). The yield is 89% of the theory.

Workup

  1. distillationis then distilled off over a column
  2. additionAfter an intermediate fraction containing methanol and ethanol as well, the excess of ethanol
  3. distillationis distilled off
  4. distillationBy distillation of the residue under reduced pressure

Sources & evidence

ORD record
ord-86f70b25e3254a199e762df53c4613e1
Source dataset
uspto-grants-1979_01
Patent number
US04135050

Reaction notes

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