(E)-N,N-dimethyl-2-(8-nitroquinolin-7-yl)ethenamine → 8-Nitro-7-quinolinecarboxaldehyde

HRID 513644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 513644
CN(C)/C=[CH:4]/[C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1.C1C[O:22]CC1.O>>[N+:15]([C:14]1[C:5]([CH:4]=[O:22])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:17])=[O:16]

Komponenten

3

Edukt 2

HCID 10586304(E)-N,N-dimethyl-2-(8-nitroquinolin-7-yl)ethenamine2×HCID 21881883Oxolane--water (1/1)

Produkt 1

HCID 117695548-Nitro-7-quinolinecarboxaldehydeAusbeute 71 %

Versuchsvorschrift

NalO4 (11.71 g, 54.76 mmol) was added portionwise to a solution of dimethyl-[(E)-2-(8-nitro-quinolin-7-yl)-vinyl]-amine (Intermediate 203) (4.44 g, 18.3 mmol) in THF/water (1:1, 70 ml). The mixture was stirred at room temperature for 16 h. The insoluble material was removed by filtration and washed with EtOAc (60 ml). The combined organic phases were washed with sat. sodium bicarbonate solution, brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (3.24 g, 71%).

Aufarbeitung

  1. customThe insoluble material was removed by filtration
  2. washwashed with EtOAc (60 ml)
  3. washThe combined organic phases were washed with sat. sodium bicarbonate solution, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c54549d621aa4308be8cf37efda606b3
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102688B2

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