Potassium Carbonate → HCID 67112502, Verbindung

HRID 341056

Reaktionsgleichung

Reaktionsgleichung von HRID 341056
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=O)[C:12]([C:21](OCC)=[O:22])=[CH:11]1.P(Cl)(Cl)(Cl)=O.[F:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[NH:38][NH2:39].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N:10]1[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2=[N:39][N:38]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[F:31])[C:21](=[O:22])[C:12]2=[CH:11]1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 4238442-Fluorophenylhydrazine hydrochlorideHCID 68153945Ethyl 1-[(2-fluoro-4-iodophenyl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate

Produkt 1

HCID 67112502HCID 67112502, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Ethyl 1-[(2-fluoro-4-iodophenyl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate (1.4 g, 3.1 mmol) was dissovled in phosphorus oxychloride (6.0 mL, 64 mmol, 21 equiv) and stirred for 2.5 hours at ambient temperature. The mixture was diluted with toluene (10 mL) and concentrated in vacuo. The residue was dissolved in dioxane (17 mL), treated with 2-fluorophenylhydrazine (0.87 g, 6.8 mmol, 2.2 equiv) and potassium carbonate (1.3 g, 9.4 mmol, 3 equiv) and stirred at ambient temperature for 5 minutes. The mixture was placed into a preheated oil bath at 80° C. for 1 hour, cooled to ambient temperature and diluted with chloroform (150 mL). The organic mixture was washed once with water (50 mL) and brine (50 mL), dried with sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with a chloroform:methanol (95:5) solution (30 mL). The solid was filtered and dried in vacuo, providing the titled compound.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dioxane (17 mL)
  3. stirringstirred at ambient temperature for 5 minutes
  4. waitThe mixture was placed into a preheated oil bath at 80° C. for 1 hour
  5. temperaturecooled to ambient temperature
  6. washThe organic mixture was washed once with water (50 mL) and brine (50 mL)
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated with a chloroform:methanol (95:5) solution (30 mL)
  11. filtrationThe solid was filtered
  12. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e08fecfcf6ce423885e283eb09c67de2
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895580B2

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