Hydrochloric Acid → HCID 13471557, compound

HRID 483186Notes

Reaction equation

HRID 483186 reaction equation
[ClH:1].[NH2:2][CH:3]([CH2:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[NH:11][C:10](=[O:19])[CH:9]=1)[C:4]([OH:6])=[O:5].[C:20](=[O:23])([O-])[O-].[K+].[K+].[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1.Cl>CC(C)=O.O>[Cl:26][C:27]1[CH:35]=[CH:34][C:30]([C:31]([NH:2][CH:3]([CH2:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][C:20](=[O:23])[C:12]4[CH:17]=[CH:16][C:15]([Cl:1])=[CH:14][CH:13]=4)[CH:16]=3)[NH:11][C:10](=[O:19])[CH:9]=2)[C:4]([OH:6])=[O:5])=[O:32])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 85014-Chlorobenzoyl chlorideHCID 11430Potassium CarbonateHCID 13471535HCID 13471535, compound

Product 1

HCID 13471557HCID 13471557, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

2.0 Grams of 2-amino-3-(6-hydroxy-2-quinolon-4-yl)propionic acid hydrochloride and 4.8 g of potassium carbonate were dissolved in 100 ml of aceton with 50 ml of water. To this mixture was added 2.7 g of p-chlorobenzoyl chloride was added dropwise under ice-cooled condition with stirring. The reaction was continued for 3 hours under ice-cooled condition with stirring. Acetone was removed by distillation, the residue obtained was diluted with water, acidified with hydrochloric acid. The crystals precipitated were collected by filtration. Recrystallized from ethanol-water to obtain 1.5 g of 2-(4-chlorobenzoylamino)3-[6-(4-chlorobenzoyloxy)-2-quinolon-4-yl]propionic acid in the form of white powdery product.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooled condition
  3. temperaturecooled condition
  4. stirringwith stirring
  5. customAcetone was removed by distillation
  6. customthe residue obtained
  7. customThe crystals precipitated
  8. filtrationwere collected by filtration
  9. customRecrystallized from ethanol-water

Sources & evidence

ORD record
ord-c887e7447eae484aab01bbd974984f0c
Source dataset
uspto-grants-1986_03
Patent number
US04578381

Reaction notes

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