Water → 2-[(3-chlorophenyl)amino]acetic Acid

HRID 2199788Notes

Reaction equation

HRID 2199788 reaction equation
C[O:2][C:3](=[O:13])[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1.[OH-].[Na+].O>C(O)C.C(OCC)(=O)C>[Cl:12][C:8]1[CH:7]=[C:6]([NH:5][CH2:4][C:3]([OH:13])=[O:2])[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 11629788HCID 11629788, compound

Product 1

HCID 37803192-[(3-chlorophenyl)amino]acetic AcidYield 86.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

(3-Chloro-phenylamino)-acetic acid methyl ester (4 g, 20.0 mmol) and sodium hydroxide (4.00 g, 100 mmol) were combined in ethanol (60.0 mL) and water (10 mL) to give a light yellow solution which was heated at 60° C. for 4 hours. The reaction mixture was cooled to ambient temperature, diluted with ethyl acetate and washed with 1M aqueous hydrochloric acid. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give (3-chloro-phenylamino)-acetic acid as a brown solid (3.20 g, 86%).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. washwashed with 1M aqueous hydrochloric acid
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-091b5b7514cd4dcfbe1446a155c6b6dc
Source dataset
uspto-grants-2016_06
Patent number
US09359345B2

Reaction notes

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