Ethanol → Ethyl 2-Amino-4-fluorobenzoate

HRID 1983504Notes

Reaction equation

HRID 1983504 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([F:11])=[CH:10][C:2]=1[NH2:1])[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 14233600Ethyl 2-Amino-4-fluorobenzoate

Procedure

A total of 10 g of 2-amino-4-fluoro-benzoic acid was dissolved in 129 ml of ethanol, 6.45 ml of sulfuric acid was added and the mixture was heated under reflux for 11 hours. After cooling to room temperature, the solvent was evaporated to about half. Water was added and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:5), to give 7.57 g of the title compound as a pale yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 11 hours
  3. customthe solvent was evaporated to about half
  4. additionWater was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe resulting organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent was evaporated
  9. customThe residue was purified
  10. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-21e01fdc09cb4322a04e000f989716b0
Source dataset
uspto-grants-2009_06
Patent number
US07541376B2

Reaction notes

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