Hydrazine → HCID 52914154, Verbindung

HRID 341029

Reaktionsgleichung

Reaktionsgleichung von HRID 341029
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=S)[C:12]([C:21](OCC)=[O:22])=[CH:11]2)=[CH:5][CH:4]=1.Cl.[F:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[NH:34][NH2:35].C(=O)([O-])[O-].[K+].[K+].NN.C(=O)(O)[O-].[Na+]>C(O)C>[F:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]1[C:21](=[O:22])[C:12]2=[CH:11][N:10]([CH2:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]2=[N:35]1

Komponenten

7

Edukt 5

HCID 9321HydrazineHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)HCID 86668672HCID 86668672, Verbindung

Produkt 1

HCID 52914154HCID 52914154, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Ethyl {[4-(methoxy)phenyl]methyl}-4-thioxo-1,4-dihydroquinoline-3-carboxylate (128 mg, 0.362 mmol), 2-fluorophenylhydrazine hydrochloride (88. mg, 0.543 mmol, 1.5 equiv) and potassium carbonate (250 mg, 1.81 mmol, 5 equiv) were combined in absolute ethanol (5 mL) and placed into an oil bath preheated at 70° C. for 14 hours. Additional hydrazine (120 mg, 1.09 mmol, 3 equiv) was added and the mixture was heated for an additional 24 hours at 70° C. The mixture was cooled to ambient temperature, poured into sodium bicarbonate (20 mL, aqueous saturated) and extracted with ethyl acetate (1×75 mL). The organic extract was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 95:5; dichloromethane:methanol), providing the titled compound: 1H-NMR (500 MHz, d6-DMSO) δ 9.10 (1H, s), 8.19 (1H, dd, J=8.0, 1.3 Hz), 7.81 (1H, d, J=8.7 Hz), 7.64-7.58 (2H, m), 7.53 (1H, t, J=7.6 Hz), 7.47-7.43 (1H, m), 7.40 (1H, ddd, J=10.2, 8.3, 1.3 Hz), 7.35-7.31 (1H, m), 7.30 (2H, d, J=8.6 Hz), 6.92 (2H, d, J=8.6 Hz), 5.66 (2H, s), 3.71 (3H, s) ppm; high resolution mass spectrometry (ES+) m/z 400.1461 [(M+H)+; calculated for C24H18FN3O2: 400.1456].

Aufarbeitung

  1. customplaced into an oil bath
  2. temperatureThe mixture was cooled to ambient temperature
  3. extractionextracted with ethyl acetate (1×75 mL)
  4. extractionThe organic extract
  5. dry with materialwas dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel gradient chromatography (100:0 to 95:5; dichloromethane:methanol)

Quellen und Nachweise

ORD-Eintrag
ord-d84b345beb3946ec90f249e9e9b589e4
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895580B2

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