Benzyl Chloride → 6-Nitro-N-benzyl-2-quinolone

HRID 751095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751095
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH:8]=[CH:7]2)([O-:3])=[O:2].[F-].[Cs+].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:9](=[O:14])[CH:8]=[CH:7]2)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 7503Benzyl ChlorideHCID 25953Cesium fluorideHCID 8999326-Nitroquinolin-2(1H)-one

Produkt 1

HCID 597543586-Nitro-N-benzyl-2-quinoloneAusbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Compound 46B (50 mg, 0.26 mmol) was dissolved in DMF (1 mL), CsF (120 mg, 0.79 mmol) and benzyl chloride (0.09 mL, 0.79 mmol) were added, and the reaction was stirred at rt for 16 h. The reaction mixture was then concentrated under reduced pressure and subsequently purified by silica gel flash chromatography eluting with 0-5% EtOAc/CH2Cl2 (gradient) to give the title compound (57 mg, 77%). LC/MS m/z 281 [M+H]+.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customsubsequently purified by silica gel flash chromatography
  3. washeluting with 0-5% EtOAc/CH2Cl2 (gradient)

Quellen und Nachweise

ORD-Eintrag
ord-787746ac2fd44961971fbd6d69d02eec
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405234B2

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