Ethyl 4-chlorobenzoate → 2-(4-Chlorobenzoylamino)-3-(2-quinolon-3-yl)propionic acid

HRID 2225342

Reaction equation

HRID 2225342 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=O)=[CH:4][CH:3]=1.CC[O-].[Na+].[NH2:17][CH:18]([CH2:22][C:23]1[C:24](=[O:33])[NH:25][C:26]2[C:31]([CH:32]=1)=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:19]([OH:21])=[O:20]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:17][CH:18]([CH2:22][C:23]2[C:24](=[O:33])[NH:25][C:26]3[C:31]([CH:32]=2)=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:19]([OH:21])=[O:20])=[O:8])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 81785Ethyl 4-chlorobenzoateHCID 2723922Sodium ethoxideHCID 133420972-Amino-3-(2-quinolon-3-yl)propionic acid

Product 1

HCID 133421032-(4-Chlorobenzoylamino)-3-(2-quinolon-3-yl)propionic acidYield 9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 100 ml of ethanol, 1.66 g of ethyl p-chlorobenzate, 0.5 g of sodium ethylate and 2.09 g of 2-amino-3-(2-quinolon-3-yl)propionic acid were added and the whole mixture was placed in an autoclave. The reaction was carried out under 110 atmospheric pressure at 140°-150° C. for 6 hours. After completion of the reaction, the reaction mixture was cooled and concentrated under a reduced pressure. The residue was dissolved in 200 ml of chloroform, washed with 1%-potassium carbonate aqueous solution, a diluted hydrochloric acid and water in this order, then the chloroform layer was dried with sodium sulfate. The solvent was removed by distillation, the residue was recrystallized from ethanol-water to obtain 300 mg of 2-(4-chlorobenzoylamino)-3-(2-quinolon-3-yl)propionic acid in the form of white powdery product.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction mixture was cooled
  3. concentrationconcentrated under a reduced pressure
  4. dissolutionThe residue was dissolved in 200 ml of chloroform
  5. washwashed with 1%-potassium carbonate aqueous solution
  6. dry with materiala diluted hydrochloric acid and water in this order, then the chloroform layer was dried with sodium sulfate
  7. customThe solvent was removed by distillation
  8. customthe residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-e1a9a765c6874c579b1f5c43c8b29d08
Source dataset
uspto-grants-1994_09
Patent number
USRE034722

Linked notes

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