Water → 2-{[2-Chloro-4-(trifluoromethyl)phenyl]amino}-3-methylbutanoic acid

HRID 462660

Reaction equation

HRID 462660 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[NH:14][CH:15]([CH:21]([CH3:23])[CH3:22])[C:16]([O:18]CC)=[O:17].O>C(O)C>[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[NH:14][CH:15]([CH:21]([CH3:23])[CH3:22])[C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 20283987Ethyl 2-(2-chloro-4-trifluoromethylphenylamino)-3-methylbutanoate

Product 1

HCID 39476432-{[2-Chloro-4-(trifluoromethyl)phenyl]amino}-3-methylbutanoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 0.60 grams of sodium hydroxide dissolved in 10 ml of ethanol was added 3.30 g of the above ester. The mixture was stirred at room temperature for 4 hours, after which water was added, and the mixture was washed with toluene. The organic phase was discarded. The product was acidified, extracted into ether, washed with water, dried and solvent removed to yield 2-(2-chloro-4-trifluoromethylphenylamino)-3-methylbutanoic acid, m.p. 132°-135°, in 90% yield.

Workup

  1. washthe mixture was washed with toluene
  2. extractionextracted into ether
  3. washwashed with water
  4. customdried
  5. customsolvent removed

Sources & evidence

ORD record
ord-ae7e67b2425643fa8e174fc101f32af8
Source dataset
uspto-grants-1985_05
Patent number
US04517130

Linked notes

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