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

HRID 483178

Reaktionsgleichung

Reaktionsgleichung von HRID 483178
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-aa6fb9ed376f4ebcb8a81c60ad956e85
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04578381

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