Sodium Hydroxide → 2-(2,3,4-Trifluoroanilino)propionic acid

HRID 458174Notes

Reaction equation

HRID 458174 reaction equation
[F:1][C:2]1[C:15]([F:16])=[C:14]([F:17])[CH:13]=[CH:12][C:3]=1[NH:4][CH:5]([CH3:11])[C:6]([O:8]CC)=[O:7].[OH-].[Na+]>C(O)C>[F:1][C:2]1[C:15]([F:16])=[C:14]([F:17])[CH:13]=[CH:12][C:3]=1[NH:4][CH:5]([CH3:11])[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22015871Ethyl 2-(2,3,4-trifluoroanilino)propionate

Product 1

HCID 220158662-(2,3,4-Trifluoroanilino)propionic acidYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-(2,3,4-trifluoroanilino)propionate (2.47 g) was dissolved in ethanol (40 ml) and an aqueous solution (3 mol/l; 10 ml) of sodium hydroxide was slowly added thereto at 0° C. After stirring at room temperature for 3 hours, the solvent was evaporated. After adding water, the residue was washed with chloroform. Next, hydrochloric acid (6 mol/l) was slowly added to the aqueous layer until pH value reached 1. Then the aqueous layer was extracted with IPE. The organic layer was dried over anhydrous magnesium sulfate and then the solvent was evaporated to give the title compound (2.19 g) as colorless crystals. Various spectral data of this product was identical with those obtained in Example 23.

Workup

  1. customat 0° C
  2. customthe solvent was evaporated
  3. additionAfter adding water
  4. washthe residue was washed with chloroform
  5. additionNext, hydrochloric acid (6 mol/l) was slowly added to the aqueous layer until pH value
  6. extractionThen the aqueous layer was extracted with IPE
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-db1c368260ee479489ff0d6b1433d084
Source dataset
uspto-grants-2007_03
Patent number
US07189847B2

Reaction notes

Loading…