Pentenone → 2,4-Dimethyl-5,6-dimethoxy-8-nitroquinoline

HRID 1863115

Reaktionsgleichung

Reaktionsgleichung von HRID 1863115
[CH3:1][O:2][C:3]1[C:9]([O:10][CH3:11])=[CH:8][C:6]([NH2:7])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.[CH3:15][C:16](=O)[CH:17]=[CH:18][CH3:19]>C1C=CC=CC=1.C(OCC)(=O)C>[CH3:11][O:10][C:9]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]2[C:8]=1[C:16]([CH3:15])=[CH:17][C:18]([CH3:19])=[N:7]2

Komponenten

4

Edukt 2

HCID 12248PentenoneHCID 46531524,5-Dimethoxy-2-nitroaniline

Produkt 1

HCID 6216122,4-Dimethyl-5,6-dimethoxy-8-nitroquinolineAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21583983Benzene ethyl acetateLösungsmittel

Versuchsvorschrift

4,5-Dimethoxy-2-nitroaniline and 3-penten-2-one were subjected to a Skraup reaction. A black, tarry substance was obtained, from which an orange solid could be isolated by chromatography over silica gel using benzene-ethyl acetate (19:1) to elute the product. That material was thrice crystallized from 2-propanol, re-chromatographed, and again crystallized to afford 14% yield of golden 5,6-dimethoxy-2,4-dimethyl-8-nitroquinoline. Although it melted 85°-108°, it showed a single spot on two tlc systems.

Aufarbeitung

  1. customA black, tarry substance was obtained, from which an orange solid
  2. customcould be isolated by chromatography over silica gel
  3. washto elute the product
  4. customcrystallized from 2-propanol
  5. customre-chromatographed
  6. customagain crystallized

Quellen und Nachweise

ORD-Eintrag
ord-39364203104b46139f0635d114ddab03
Quelldatensatz
uspto-grants-1979_09
Patentnummer
US04167638

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