Reaktionsgleichung
C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O[C:15](=[O:31])[C:16](=[CH:22][NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[I:30])[C:17]([O:19][CH2:20][CH3:21])=[O:18])C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:20]([O:19][C:17]([C:16]1[C:15](=[O:31])[C:29]2[C:24](=[C:25]([I:30])[CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)=[O:18])[CH3:21]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
In a 2-neck round bottomed flask (250 mL), phenylether (60 mL) was put to reflux on a heating mantel. When it started boiling, p-toluenesulfonic acid (0.140 g) was added. 2-[(2-iodo-phenylamino)-methylene]-malonic acid diethyl ester was dissolved in phenylether (20 mL) and the mixture was poured into the boiling solvent. The mixture was refluxed for 3 h. The crude was transferred to a bequer and cooled to room temperature. Hexanes (600 mL) were added and a precipitate was observed. The mixture was stirred for 5 min, followed by filtration of the solid and thorough wash with hexanes to afford 8-iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester as a grayish solid (2 g, 46%). 1H NMR (DMSO-d6, 400MHz) δ 1.43 (t, 3H), 4.39 (q, 2H), 7.36 (t, 1H), 8.32 (d, 1H), 8.37 (d, 1H), 8.63 (s, 1H), 11.4 (s, 1H). Exact mass calculated for C12H10INO3 342.97, found 343.9 (MH+).
Aufarbeitung
- temperatureto reflux on a heating mantel
- additionthe mixture was poured into the boiling solvent
- temperatureThe mixture was refluxed for 3 h
- filtrationfollowed by filtration of the solid
- washthorough wash with hexanes
Quellen und Nachweise
- ORD-Eintrag
- ord-ba9644a77b19470482f8cc169586e030
- Quelldatensatz
- uspto-grants-2009_12
- Patentnummer
- US07625906B2
Verknüpfte Notizen
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