Water → N-methyl-N-(2-carboxybenzyl)-4-carboxymethylaniline

HRID 904183Notes

Reaction equation

HRID 904183 reaction equation
[CH3:1][N:2]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([O:24]CC)=[O:23])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12]CC)=[O:11])=[CH:5][CH:4]=1.[OH-].[Na+].O>C(O)C>[CH3:1][N:2]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([OH:24])=[O:23])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 23333616HCID 23333616, compound

Product 1

HCID 23333576N-methyl-N-(2-carboxybenzyl)-4-carboxymethylanilineYield 72.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The oily ester (20 g) so obtained was added to a solution of sodium hydroxide (25 g) in a mixed liquor of water (300 ml) and ethanol (100 ml). The mixture was heated under reflux for 2 hours. After most of ethanol was distilled off, the mixture was washed with ether. The aqueous layer was acidified by addition of acetic acid to the layer cooled with ice, and then extracted with ether. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was recrystallized from methanol-benzene to obtain N-methyl-N-(2-carboxybenzyl)-4-carboxymethylaniline (12.2 g) as colorless prismatic crystals.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. distillationAfter most of ethanol was distilled off
  4. washthe mixture was washed with ether
  5. additionThe aqueous layer was acidified by addition of acetic acid to the layer
  6. temperaturecooled with ice
  7. extractionextracted with ether
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off
  10. customThe residue was recrystallized from methanol-benzene

Sources & evidence

ORD record
ord-ed863102f49a4e24a6bc024b42e40aef
Source dataset
uspto-grants-1980_10
Patent number
US04230703

Reaction notes

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