Potassium Carbonate → HCID 178515185, Verbindung

HRID 341061

Reaktionsgleichung

Reaktionsgleichung von HRID 341061
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=[C:3]1[C:12]([O:14]CC)=O.P(Cl)(Cl)(Cl)=O.[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][NH2:30].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[C:12](=[O:14])[C:3]2=[CH:4][NH:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]2=[N:30]1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 220876Ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylateHCID 4238442-Fluorophenylhydrazine hydrochloride

Produkt 1

HCID 178515185HCID 178515185, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate (3.8 g, 17 mmol) was dissolved in phosphorus oxychloride (25 mL, 0.26 mol, 15 equiv) and stirred at ambient temperature for 14 hours. The mixture was concentrated in vacuo and the residue was concentrated from toluene (3×25 mL). The resulting residue was dissolved in 1,2-dimethoxyethane (60 mL) and degassed N,N-dimethylformamide (10 mL) and treated with 2-fluorophenylhydrazine (4.4 g, 35 mmol, 2 equiv) and potassium carbonate (12 g, 87 mmol, 5 equiv). The mixture was placed into a preheated oil bath at 80° C. for 14 hours. The mixture was cooled to ambient temperature, diluted with water (100 mL) and ethyl acetate (100 mL) and filtered. The solid was collected and dried in vacuo, providing the titled compound as a yellow solid.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. concentrationthe residue was concentrated from toluene (3×25 mL)
  3. dissolutionThe resulting residue was dissolved in 1,2-dimethoxyethane (60 mL)
  4. customdegassed N,N-dimethylformamide (10 mL)
  5. waitThe mixture was placed into a preheated oil bath at 80° C. for 14 hours
  6. temperatureThe mixture was cooled to ambient temperature
  7. filtrationfiltered
  8. customThe solid was collected
  9. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2fb7e142bd944a25baabe0eeeb5d94ca
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895580B2

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