Dimethylformamide → Ethyl 1-ethyl-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 2099124Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2099124
[I:1][C:2]1[CH:3]=[C:4]2C(=[CH:10][CH:11]=1)NC=[C:6]([C:12]([OH:14])=[O:13])[C:5]2=[O:15].[C:16](=O)([O-])[O-].[K+].[K+].I[CH2:23][CH3:24].[CH3:25][N:26]([CH:28]=O)[CH3:27]>C(OCC)(=O)C>[CH2:23]([O:14][C:12]([C:6]1[C:5](=[O:15])[C:4]2[C:27](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=2)[N:26]([CH2:25][CH3:16])[CH:28]=1)=[O:13])[CH3:24]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 7196836-Iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Produkt 1

HCID 57720090Ethyl 1-ethyl-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 1,4-dihydro-6-iodo-4-oxo-quinoline-3-carboxylic acid (J. Ellis, E. Gellert, J. Robson, Aust. J. Chem., 1973, 26, 907) (3.15 g, 10 mmol), potassium carbonate (6.9 g, 50 mmol) and iodoethane (15.6 g, 100 mmol) in dry DMF was heated at 70° C. with vigorous stirring. After 16 h the mixture was cooled and diluted with ethyl acetate. The resultant mixture was washed with water and the organic phase separated, dried and evaporated to yield the title compound as pale yellow solid, 1H NMR δ (CDCl3) 1.41 (3H, t, J=7.1 Hz), 1.54 (3H, t, J=7.3 Hz), 4.23 (2H, q, J=7.2 Hz), 4.40 (2H, q, J=7.1 Hz), 7.20 (1H, d, J=8.9 Hz), 7.95 (1H, dd, J=2.1 & 8.9 Hz), 8.48 (1H, s), 8.86 (1H, d, J=2.1 Hz).

Aufarbeitung

  1. temperatureAfter 16 h the mixture was cooled
  2. washThe resultant mixture was washed with water
  3. customthe organic phase separated
  4. customdried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c2c5518626c140e69c12ad21c34b394b
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569550B2

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