Sodium Hydroxide → 2-((4-Chlorophenyl)amino)acetic acid

HRID 1402841

Reaction equation

HRID 1402841 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 302644Glycine, N-(4-chlorophenyl)-, ethyl ester

Product 1

HCID 2307172-((4-Chlorophenyl)amino)acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To the suspension of ethyl N-(4-chlorophenyl)-glycinate (10.4 g) in ethanol (4 ml) the solution of NaOH (4 g) in water (40 ml) was added. Upon heating a clear solution is formed, which is refuxed for 0.5 h. The solution is decolorized with activated carbon and filtered while hot. The filtrate is cooled in an ice bath and conc. HCl (5 ml) is added dropwise with stirring (pH 1-2). The precipitate formed is collected by suction filtration and washed with water. After drying in vacuo N-(4-chlorophenyl)-glycine (6.51 g) is obtained as colourless crystals.

Workup

  1. additionwas added
  2. temperatureUpon heating a clear solution
  3. customis formed
  4. filtrationfiltered while hot
  5. temperatureThe filtrate is cooled in an ice bath
  6. additionconc. HCl (5 ml) is added dropwise
  7. customThe precipitate formed
  8. filtrationis collected by suction filtration
  9. washwashed with water
  10. dry with materialAfter drying in vacuo N-(4-chlorophenyl)-glycine (6.51 g)
  11. customis obtained as colourless crystals

Sources & evidence

ORD record
ord-eb77f9c75a8d4d51aed09c4e87f57389
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Linked notes

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