Sodium Hydroxide → Benzoic Acid

HRID 1596234Notes

Reaction equation

HRID 1596234 reaction equation
C(N1CCN(NC([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)=O)CC1)(=O)C.[OH-].[Na+]>CO>[C:17]([OH:19])(=[O:18])[C:16]1[CH:21]=[CH:22][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21701664HCID 21701664, compound

Product 1

HCID 243Benzoic AcidYield 241.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 4-[N-(4-acetyl-1-piperazinyl)carbamoyl]benzoate (300 mg) in methanol (9 ml) was added 1N aqueous solution of sodium hydroxide (1.2 ml) at ambient temperature and the mixture was stirred at the same temperature for 10 hours. After evaporation of solvent, the residue was diluted with water and neutralized with 1N hydrochloric acid and extracted with a mixture of ethyl acetate and tetrahydrofuran. The organic layer was dried over magnesium sulfate and concentrated. The residue was washed with tetrahydrofuran and ethyl acetate to give 4-N-(4-acetyl-1-piperazinyl)carbamoyl]benzoic acid (290 mg).

Workup

  1. customAfter evaporation of solvent
  2. additionthe residue was diluted with water and neutralized with 1N hydrochloric acid
  3. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated
  6. washThe residue was washed with tetrahydrofuran and ethyl acetate

Sources & evidence

ORD record
ord-9d321688fd14497ea421e1e04a806d90
Source dataset
uspto-grants-2001_09
Patent number
US06291464B1

Reaction notes

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