N-bromobutanimide → [(8-Bromo-1,2,3,4-tetrahydro-6-nitro-5-quinolinyl)-amino]oxo-acetic Acid Ethyl Ester

HRID 48241Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 48241
[CH2:1]([O:3][C:4](=[O:21])[C:5]([NH:7][C:8]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12][NH:13]2)=[O:6])[CH3:2].[Br:22]N1C(=O)CCC1=O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:21])[C:5]([NH:7][C:8]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][C:15]([Br:22])=[C:14]2[C:9]=1[CH2:10][CH2:11][CH2:12][NH:13]2)=[O:6])[CH3:2]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 10334564[(1,2,3,4-Tetrahydro-6-nitro-5-quinolinyl)amino]oxo-acetic Acid Ethyl Ester

Produkt 1

HCID 10474405[(8-Bromo-1,2,3,4-tetrahydro-6-nitro-5-quinolinyl)-amino]oxo-acetic Acid Ethyl EsterAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of the product from Example 87 (0.15 g, 0.5 mmol) and N-bromosuccinimide (0.23 g, 1 mmol) in 2 mL dimethylformamide was stirred at room temperature for 18 hours. The solution was poured onto methylene chloride/water and separated and the water layer back extracted with methylene chloride. The combined organic layers were washed with water, dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (4:1 to 1:1 heptane:ethyl acetate as eluant) to give the title compound (0.15 g, 81% yield).

Aufarbeitung

  1. additionThe solution was poured onto methylene chloride/water
  2. customseparated
  3. extractionthe water layer back extracted with methylene chloride
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by silica gel chromatography (4:1 to 1:1 heptane:ethyl acetate as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-4371e4c6c5364e52a692bc88fa9d0ae1
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703391B2

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