Ethanol → Ethyl 2-(4-(dimethylcarbamoyl)phenyl)-3-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1467675Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1467675
[CH3:1][N:2]([CH3:23])[C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[N:11]/[C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH2:14][O:15][C:16]3=[O:21])=[CH:6][CH:5]=1.[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1.[Na].[C:34](OCC)(=[O:37])CC.[CH2:41](O)C>>[CH3:1][N:2]([CH3:23])[C:3]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH:29]([C:28]3[CH:31]=[CH:32][C:25]([F:24])=[CH:26][CH:27]=3)[C:34](=[O:37])[C:13]3[C:17]([C:16]([O:15][CH2:14][CH3:41])=[O:21])=[CH:18][CH:19]=[CH:20][C:12]=3[NH:11]2)=[CH:6][CH:5]=1)=[O:22]

Komponenten

6

Edukt 5

HCID 702EthanolHCID 7749Ethyl PropionateHCID 680234-FluorobenzaldehydeHCID 5360545SodiumHCID 178484438HCID 178484438, Verbindung

Produkt 1

HCID 67261345Ethyl 2-(4-(dimethylcarbamoyl)phenyl)-3-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylateAusbeute 22 %

Versuchsvorschrift

Compound (E)-N,N-dimethyl-4-((1-oxo-1,3-dihydroisobenzofuran-4-ylimino)methyl)benzamide (1.36 g, 4.4 mmol), 4-fluorobenzaldehyde (600 mg, 4.84 mmol), sodium (405 mg, 17.6 mmol), ethanol (40 mL) and ethyl propionate (66 mL) were added and the mixture was stirred at room temperature overnight. Then the resulting mixture was evaporated under reduced pressure and extracted with ethyl acetate (100 mL×4) and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 5:1) to give the title compound as a solid (490 mg, yield 22%). LC-MS (ESI) m/z: 461 (M+1)+.

Aufarbeitung

  1. customThen the resulting mixture was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate (100 mL×4)
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-59a523c7fb9e49f7aa5d035c70659f2d
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999987B2

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