Dimethylcarbamoyl Chloride → 5,6,7,8-Tetrahydroquinoline-2-carbonitrile

HRID 499391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499391
[N+:1]1([O-])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C[Si]([C:16]#[N:17])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O>[C:16]([C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[N:1]=1)#[N:17]

Komponenten

5

Edukt 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 27781345,6,7,8-Tetrahydro-1-quinoliniumolate

Produkt 1

HCID 114464875,6,7,8-Tetrahydroquinoline-2-carbonitrileAusbeute 17,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6587NitroethaneLösungsmittel

Versuchsvorschrift

5,6,7,8-Tetrahydroquinoline N-oxide (3.0 g, 19.1 mmol) was dissolved in nitroethane (30 ml), and trimethylsilyl cyanide (2.1 g, 21.0 mmol) and N,N-dimethylcarbamoyl chloride (2.1 g, 19.1 mmol) were added thereto. The reaction mixture was stirred at room temperature for 3 days, concentrated under reduced pressure, combined with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried. The solvent was evaporated under reduced pressure. The residue was subjected to a silica gel column chromatography and eluted with hexane-ethyl acetate (2:1, v/v) to give the titled compound (0.52 g, 17%).

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. washeluted with hexane-ethyl acetate (2:1

Quellen und Nachweise

ORD-Eintrag
ord-2d8b371bf17f4466a504228477791283
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767665B2

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