Water → HCID 57765303, Verbindung

HRID 2061849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2061849
[F:1][C:2]1[CH:3]=[C:4]([I:18])[CH:5]=[C:6]2[C:11]=1[NH:10][CH:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]2=[O:17].C(=O)([O-])[O-].[K+].[K+].I[CH2:26][CH2:27][OH:28].O>CN(C)C=O.[Cl-].[Na+].O>[F:1][C:2]1[CH:3]=[C:4]([I:18])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:26][CH2:27][OH:28])[CH:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]2=[O:17]

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12225IodoethanolHCID 18753050HCID 18753050, Verbindung2×

Produkt 1

HCID 57765303HCID 57765303, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Ethyl 8-fluoro-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (Intermediate 11, 7.22 g, 20 mmol) was dissolved in dimethylformamide (35 ml). Powdered potassium carbonate (8.28 g, 60 mmol) and 2-iodoethanol (11.3 ml, 145 mmol) were then added and the reaction mixture was allowed to stir at 90° C. for 1 h. The reaction mixture was cooled to room temperature and poured into brine (300 ml) then water (50 ml) was added to dissolve the material. This solution was extracted with 9:1 tetrahydrofuran:methyl tert-butyl ether (5×200 ml). The organic extracts were combined washed with brine (2×200 ml), dried over sodium sulfate, and concentrated under reduced pressure to give a dark yellow oil of ethyl 8-fluoro-1-(2-hydroxyethyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate that was carried on to the next reaction without any further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. dissolutionto dissolve the material
  3. extractionThis solution was extracted with 9:1 tetrahydrofuran
  4. washThe organic extracts were combined washed with brine (2×200 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-37205679ebeb43e598d31cc6c290f32f
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08283361B2

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