Sodium Hydroxide → N-Methyl-N-phenyl-glycine

HRID 465468

Reaction equation

HRID 465468 reaction equation
C[O:2][C:3](=[O:13])[CH2:4][N:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6].[OH-].[Na+]>O.CO>[CH3:6][N:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:4][C:3]([OH:13])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14645370Methyl 2-(methyl(phenyl)amino)acetate

Product 1

HCID 420843N-Methyl-N-phenyl-glycine

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To 500 ml of water/methanol (1/4 weight ratio), 30 g of N-phenyl-N-methylglycine methyl ester and 12.3 g (1.1 equivalent weight) of NaOH were added and refluxed for 2 hours. The methanol was evaporated from the reaction mixture under reduced pressure. Then, water was added thereto and unreacted starting materials were extracted with methylene chloride. Subsequently, 10% hydrochloric acid was added to the aqueous layer to adjust the pH at about 5, followed by extraction with ether. The ether layer wad dried, and solvent distilled to yield N-methyl-N-phenylglycine in 27.1 g.

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe methanol was evaporated from the reaction mixture under reduced pressure
  3. additionThen, water was added
  4. extractionwere extracted with methylene chloride
  5. additionSubsequently, 10% hydrochloric acid was added to the aqueous layer
  6. extractionfollowed by extraction with ether
  7. dry with materialThe ether layer wad dried
  8. distillationsolvent distilled

Sources & evidence

ORD record
ord-e04ac19290ef423a918068f912bdf195
Source dataset
uspto-grants-1992_10
Patent number
US05153236

Linked notes

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