Potassium Hydroxide → HCID 18786977, compound

HRID 1107381Notes

Reaction equation

HRID 1107381 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][N:6]([CH3:22])[C:7](=[O:21])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])C.[OH-].[K+]>CO.O>[CH3:22][N:6]([C:7](=[O:21])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])[CH2:5][C:4]([OH:23])=[O:3]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18786983HCID 18786983, compound

Product 1

HCID 18786977HCID 18786977, compoundYield 48.9%

Reagents, catalysts & solvents 1

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

Procedure

N-methyl-N-[2-(methylphenyl)benzoyl]glycine ethyl ester (4.5 g, 14.45 mmol) and KOH (2.43 g, 43.4 mmol) in MeOH/H2O (200 mL/50 mL) were heated at reflux for 45 minutes. The solvent was removed and the residue dissolved in H2O. The aqueous solution was washed with Et2O and acidified with HCl (10%). The acidified aqueous layer was extracted with EtOAc, the EtOAc extract was washed with brine (2×), dried over (MgSO4) and evaporated. There was obtained N-methyl-N-[2-(methylphenyl)benzoyl]glycine (2.0 g); LRMS (M+H)+=284.1, (M+NH4)+=301.1

Workup

  1. temperatureat reflux for 45 minutes
  2. customThe solvent was removed
  3. dissolutionthe residue dissolved in H2O
  4. washThe aqueous solution was washed with Et2O
  5. extractionThe acidified aqueous layer was extracted with EtOAc
  6. extractionthe EtOAc extract
  7. washwas washed with brine (2×)
  8. dry with materialdried over (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-b4ed425bc6bb4fafbf4e415008c9c125
Source dataset
uspto-grants-2000_05
Patent number
US06060462

Reaction notes

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