Ammonia → 2-(4-Chlorobenzoylamino)-3-(2-quinolon-4-yl)propionamide

HRID 483187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 483187
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][CH:9]([CH2:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16](=[O:24])[CH:15]=2)[C:10]([OH:12])=O)=[O:7])=[CH:4][CH:3]=1.C([N:29](CC)CC)C.ClC(OCC(C)C)=O.N>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH:9]([CH2:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16](=[O:24])[CH:15]=2)[C:10]([NH2:29])=[O:12])=[O:7])=[CH:25][CH:26]=1

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 5042RebamipideHCID 8471TriethylamineHCID 62365Isobutyl chloroformate

Produkt 1

HCID 134715702-(4-Chlorobenzoylamino)-3-(2-quinolon-4-yl)propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

1.8 Grams of 2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionic acid was dissolved in 80 ml of N,N-dimethylformamide. To this solution was added 0.6 g of triethylamine. Then, under ice-cooled condition with stirring, 0.8 g of isobutyl chloroformate was added to the above-mentioned mixture. At the same temperature condition, 10 ml of N,N-dimethylformamide solution containing 0.4 g of ammonia was added dropwise to the reaction mixture, and stirred for 3 hours. After the removal of N,N-dimethylformamide by distillation, water was added to the residue and the crystals precipitated were collected by filtration, and were washed with an aqueous solution of sodium hydroxide. Recrystallized from dimethylformamide-water to obtain 0.7 g of 2-(4-chlorobenzoylamino)-3-(2-quinolon-4-yl)propionamide in the form of light yellowish powdery product.

Aufarbeitung

  1. temperatureThen, under ice-cooled condition
  2. additionwas added dropwise to the reaction mixture
  3. stirringstirred for 3 hours
  4. customAfter the removal of N,N-dimethylformamide
  5. distillationby distillation, water
  6. additionwas added to the residue
  7. customthe crystals precipitated
  8. filtrationwere collected by filtration
  9. washwere washed with an aqueous solution of sodium hydroxide
  10. customRecrystallized from dimethylformamide-water

Quellen und Nachweise

ORD-Eintrag
ord-af07915151fb4bf68ed53ee5cf365a44
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04578381

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