Citric Acid → N-Methyl-N-phenyl-glycine

HRID 2184087

Reaction equation

HRID 2184087 reaction equation
[CH3:1][N:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6]CC)=[O:5].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH3:1][N:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 265936(Methyl-phenyl-amino)-acetic acid ethyl ester

Product 1

HCID 420843N-Methyl-N-phenyl-glycine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of step 1 (1.1 g, 5.6 mmol) was dissolved in methanol (50 mL) and 1M NaOH (17 mL) added. Allow reaction mixture to stir at ambient temperature over 18 hours. 10% Citric acid solution was added until a pH=4 was reached. Extract several times with EtOAc. The organic layer was washed several times with brine, dried (Na2SO4), filtered, and concentrated affording a quantitative yield of the title compound as a yellow oil. MS (ES+) m/z 166 (MH+).

Workup

  1. customAllow reaction mixture
  2. extractionExtract several times with EtOAc
  3. washThe organic layer was washed several times with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-03fbe0f0d40340a7bc7bf134029aebc9
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Linked notes

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