Lithium Hydroxide → 2-(3,4-Dichloro-phenylamino)-propionic Acid

HRID 1096189Notes

Reaction equation

HRID 1096189 reaction equation
C([O:3][C:4](=[O:16])[CH:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=1)[CH3:6])C.[Li+].[OH-]>C1COCC1.CO.O>[Cl:15][C:10]1[CH:9]=[C:8]([NH:7][CH:5]([CH3:6])[C:4]([OH:16])=[O:3])[CH:13]=[CH:12][C:11]=1[Cl:14]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69148082-(3,4-Dichloro-phenylamino)-propionic Acid ethyl ester

Product 1

HCID 69164262-(3,4-Dichloro-phenylamino)-propionic AcidYield 82.1%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A mixture of 2-(3,4-dichloro-phenylamino)-propionic acid ethyl ester (10.0 g, 38.1 mmol) and LiOH (2.74 g, 114 mmol) in THF/MeOH/water 2:1:1 (100 mL) was heated at reflux for 3 h, then after cooling poured onto water and extracted with TBME. The organic phase was extracted twice with 1 M aq. sodium hydroxide solution. The aqueous phases were combined, acidified to pH 2-3 by addition of 37% aq. HCl solution, and extracted with EtOAc. The organic layer was dried (MgSO4), filtered, and evaporated to produce the title compound (7.32 g, 82%). Light yellow solid, MS: 233.9 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. temperatureafter cooling
  4. additionpoured onto water
  5. extractionextracted with TBME
  6. extractionThe organic phase was extracted twice with 1 M aq. sodium hydroxide solution
  7. additionacidified to pH 2-3 by addition of 37% aq. HCl solution
  8. extractionextracted with EtOAc
  9. dry with materialThe organic layer was dried (MgSO4)
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-edcb9a5c9507452aacb2812978efe5d3
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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