Sodium hydride → Ethyl-8-chloro-1-(4-iodobenzyl)-4-oxo-1,4-dihydrocinnoline-3-carboxylate

HRID 449975Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 449975
[CH2:1]([O:3][C:4](=[O:18])[C:5](=[N:16][NH2:17])[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=1F)=[O:7])[CH3:2].[I:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1.[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O.O>[CH2:1]([O:3][C:4]([C:5]1[C:6](=[O:7])[C:8]2[C:9](=[C:10]([Cl:14])[CH:11]=[CH:12][CH:13]=2)[N:17]([CH2:24][C:23]2[CH:26]=[CH:27][C:20]([I:19])=[CH:21][CH:22]=2)[N:16]=1)=[O:18])[CH3:2]

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 9542584-Iodobenzyl bromideHCID 178472855ethyl 3-(3-chloro-2-fluorophenyl)-2-hydrazinylidene-3-oxopropanoate

Produkt 1

HCID 68755685Ethyl-8-chloro-1-(4-iodobenzyl)-4-oxo-1,4-dihydrocinnoline-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Ethyl-3-(3-chloro-2-fluorophenyl)-2-hydrazinylidene-3-oxopropanoate [(Example 60, Step 2) 1.61 g, 5.90 mmol] and 4-iodobenzyl bromide (2.28 g, 7.68 mmol, 1.3 equiv) were dissolved in degassed N,N-dimethylformamide (20 mL), cooled to 0° C. and treated with sodium hydride (378 mg, 9.45 mmol, 1.6 equiv). After stirring for 2 hours at 0° C., the mixture was treated with ammonium chloride (25 mL, 25% aqueous), warmed to ambient temperature, diluted with water (100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed once with water and brine, dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 20:80; hexanes:ethyl acetate), providing the titled compound.

Aufarbeitung

  1. temperaturewarmed to ambient temperature
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic extracts were washed once with water and brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel gradient chromatography (100:0 to 20:80; hexanes:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-143f2776854f458c9d7571b1dac8a58b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486946B2

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