Hydrochloric Acid → HCID 13342155, compound

HRID 483175Notes

Reaction equation

HRID 483175 reaction equation
Cl.[NH2:2][CH:3]([CH2:7][C:8]1[C:9](=[O:20])[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([O:18][CH3:19])=[CH:13][CH:12]=2)[C:4]([OH:6])=[O:5].[OH-].[Na+].[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1.Cl>O>[Cl:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH:2][CH:3]([CH2:7][C:8]2[C:9](=[O:20])[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([O:18][CH3:19])=[CH:13][CH:12]=3)[C:4]([OH:6])=[O:5])=[O:29])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 85014-Chlorobenzoyl chloride2×HCID 14798Sodium Hydroxide2×HCID 13342125HCID 13342125, compound

Product 1

HCID 13342155HCID 13342155, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.5 Grams of 2-amino-3-(6-methoxy-2-quinolon-3-yl)propionic acid hydrochloride was dissolved in a solution containing 0.8 g of sodium hydroxide in 25 ml of water, then under ice-cooled condition, 1 g of p-chlorobenzoyl chloride was added dropwise with stirring. The reaction was carried out by adding 1N-sodium hydroxide aqueous solution and p-chlorobenzoyl chloride properly, until the starting material os disappeared from the reaction mixture by checking a sample of the reaction mixture through a thin-layer-chromatograph. After completion of the reaction, the reaction mixture was acidified with hydrochloric acid, the crystals precipitated were collected by filtration. The crystals were washed with ether, then recrystallized from methanol-water to obtain 0.7 g of 2-(4-chlorobenzoylamino)-3-(6-methoxy-2-quinolon-3-yl)propionic acid in the from of yellowish powdery product.

Workup

  1. additionwas added dropwise
  2. customAfter completion of the reaction
  3. customthe crystals precipitated
  4. filtrationwere collected by filtration
  5. washThe crystals were washed with ether
  6. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-68b9f58319c94575a792fa2b9d43c902
Source dataset
uspto-grants-1986_03
Patent number
US04578381

Reaction notes

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