Ethanol → Ethyl 2-(4-(dimethylcarbamoyl)phenyl)-3-(1-methyl-1H-imidazol-2-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1968031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1968031
[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.[CH3:24][N:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH:30]=O.[Na].[CH2:33]([OH:35])[CH3:34]>C(OCC)(=O)CC>[CH3:23][N:2]([CH3:1])[C:3]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH:30]([C:26]3[N:25]([CH3:24])[CH:29]=[CH:28][N:27]=3)[C:14](=[O:15])[C:13]3[C:17]([C:16]([O:35][CH2:33][CH3:34])=[O:21])=[CH:18][CH:19]=[CH:20][C:12]=3[NH:11]2)=[CH:6][CH:5]=1)=[O:22]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5360545SodiumHCID 178484438HCID 178484438, Verbindung

Produkt 1

HCID 67261992Ethyl 2-(4-(dimethylcarbamoyl)phenyl)-3-(1-methyl-1H-imidazol-2-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylateAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7749Ethyl PropionateLösungsmittel

Versuchsvorschrift

(E)-N,N-Dimethyl-4-((1-oxo-1,3-dihydroisobenzofuran-4-ylimino)methyl)benzamide (924 mg, 3.0 mmol), 1-methyl-1H-imidazole-2-carbaldehyde (363 mg, 3.3 mmol), sodium (276 mg, 12 mmol) in ethanol (30 mL) and ethyl propionate (45 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 1:2) to afford the title compound as a yellow solid (500 mg, yield 37%). LC-MS (ESI) m/z: 447 (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 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-241a4285d8454c76b9c8566d5a451e08
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420650B2

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