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

HRID 458173Notes

Reaction equation

HRID 458173 reaction equation
[F:1][C:2]1[C:14]([F:15])=[C:13]([F:16])[CH:12]=[CH:11][C:3]=1[NH:4][CH:5]([CH3:10])[C:6]([O:8]C)=[O:7].[OH-].[Li+]>CO>[F:1][C:2]1[C:14]([F:15])=[C:13]([F:16])[CH:12]=[CH:11][C:3]=1[NH:4][CH:5]([CH3:10])[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 22015876Methyl2-(2,3,4-trifluoroanilino)propionate

Product 1

HCID 220158662-(2,3,4-Trifluoroanilino)propionic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(2,3,4-trifluoroanilino)propionate (46.64 g) was dissolved in methanol (130 ml) and an aqueous solution (3 mol/l; 100 ml) of lithium 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 diisopropyl ether (IPE). The organic layer was dried over anhydrous magnesium sulfate and then the solvent was evaporated to give the title compound (43.7 g) as colorless crystals.

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 diisopropyl ether (IPE)
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9313fa133177443dbb38304742b389ff
Source dataset
uspto-grants-2007_03
Patent number
US07189847B2

Reaction notes

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