Hydrochloric Acid → HCID 178428133, Verbindung

HRID 49198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 49198
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]1[CH2:18][C:17]2[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]=2[C:11](=O)[CH2:10]1.[C:21]([NH:24][NH2:25])([NH2:23])=[NH:22].Cl.Cl.O>C(O)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]1[CH2:18][C:17]2[N:16]=[CH:15][CH:14]=[C:13]([CH3:19])[C:12]=2[C:11](=[N:25][NH:24][C:21]([NH2:23])=[NH:22])[CH2:10]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 117482737-(2-Chloro-5-fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneHCID 178418668HCID 178418668, Verbindung

Produkt 1

HCID 178428133HCID 178428133, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 7-(2-chloro-5-fluorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one in ethanol (10 ml) was combined with aminoguanidine hydrochloride (0.041 g), concentrated hydrochloric acid (0.078 ml) and water (0.078 ml), and the mixture was heated under reflux for 4 hours. The solvent was distilled off under reduced pressure, and the residue was combined with water and the aqueous layer was washed with ethyl acetate. The aqueous layer was made alkaline with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in 1N hydrochloric acid (1 ml) and concentrated. The resultant crystal was recrystallized from ethanol-ethyl acetate to obtain 7-(2-chloro-5-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline hydrochloride (Compound G) (0.05 g) as a colorless crystal.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. washthe aqueous layer was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed successively with water and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe residue was dissolved in 1N hydrochloric acid (1 ml)
  10. concentrationconcentrated
  11. customThe resultant crystal was recrystallized from ethanol-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-95fab42f68de4fb9a9a1fcd6b5d81751
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706732B1

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