Sodium Hydroxide → HCID 22405058, compound

HRID 441239Notes

Reaction equation

HRID 441239 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[NH:13][C:14](=[O:28])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27])[C:5]([O:7]CC)=[O:6].[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[NH:13][C:14](=[O:28])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:27])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22405070HCID 22405070, compound

Product 1

HCID 22405058HCID 22405058, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of ethyl 3-chloro-4-[2-(2-methylphenyl)-benzoylamino]benzoate (4.0 g), 1N sodium hydroxide aqueous solution (15 ml) and ethanol (30 ml) was stirred for 5 hours at ambient temperature. Ethanol was removed in vacuo and the residue was washed with diethyl ether and the aqueous layer was acidified with 1N hydrochloric acid and diluted with ethyl acetate. The solution was washed with brine and dried over magnesium sulfate. Filtering and the removal of solvent afforded crude 3-chloro-4 [2-(2-methylphenyl)benzoylamino]benzoic acid (3.1 g).

Workup

  1. customEthanol was removed in vacuo
  2. washthe residue was washed with diethyl ether
  3. additiondiluted with ethyl acetate
  4. washThe solution was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltering
  7. customthe removal of solvent

Sources & evidence

ORD record
ord-f1e3a441d9b142ffa351cc54c5072735
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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