Sodium Hydroxide → 2-Dimethylamino-3-benzoylphenylacetic Acid

HRID 2051878Notes

Reaction equation

HRID 2051878 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]1[C:8]([C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:17][C:18]([O:20]C)=[O:19].[OH-].[Na+]>O.C(O)(=O)C>[CH3:22][N:2]([CH3:1])[C:3]1[C:8]([C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:17][C:18]([OH:20])=[O:19]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12901251Methyl 2-dimethylamino-3-benzoylphenylacetate

Product 1

HCID 129012542-Dimethylamino-3-benzoylphenylacetic Acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 500 mg. (1.85 mmole) of methyl 2-dimethylamino-3-benzoylphenylacetate and 15 ml. of 3 N sodium hydroxide was refluxed for 1.5 hr. under nitrogen. The cooled filtered reaction mixture was diluted with an equal volume of water and neutralized with glacial acetic acid. The precipitate which formed could not be recrystallized and was therefore dissolved in benzene and placed on a magnesium silicate column. The column was eluted with benzene-acetone to give 300 mg. of product which melted at 144°-146° C. after recrystallization from benzene-isooctane.

Workup

  1. additionA mixture of 500 mg
  2. filtrationThe cooled filtered
  3. customreaction mixture
  4. customThe precipitate which formed could not
  5. custombe recrystallized
  6. dissolutionwas therefore dissolved in benzene
  7. washThe column was eluted with benzene-acetone
  8. customto give 300 mg
  9. customof product which melted at 144°-146° C. after recrystallization from benzene-isooctane

Sources & evidence

ORD record
ord-0cc89cb303bd435db8a97d943311bc23
Source dataset
uspto-grants-1980_01
Patent number
US04182774

Reaction notes

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