1-Chloro-2,6-dinitrobenzene → 4-(2,6-Dinitrobenzylidene)-1-ethyl-1,4-dihydroquinoline

HRID 1287183Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1287183
[I-].[CH2:2]([N+:4]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:7]([CH3:8])=[CH:6][CH:5]=1)[CH3:3].Cl[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][C:17]=1[N+:25]([O-:27])=[O:26].C(N(C(C)C)CC)(C)C>C(#N)C>[N+:22]([C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:25]([O-:27])=[O:26])[C:16]=1[CH:8]=[C:7]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:4]([CH2:2][CH3:3])[CH:5]=[CH:6]1)([O-:24])=[O:23]

Komponenten

5

Edukt 3

HCID 118141-Chloro-2,6-dinitrobenzeneHCID 69062Quinolinium, 1-ethyl-4-methyl-, iodide (1:1)HCID 81531Diisopropylethylamine

Produkt 1

HCID 540122044-(2,6-Dinitrobenzylidene)-1-ethyl-1,4-dihydroquinolineAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1-Ethyllepidinium iodide (3.0 g., 10 mmole) and 1-chloro-2,6-dinitrobenzene (2.5 g., 12 mmole) are warmed in acetonitrile (50 ml.) and diisopropylethylamine (2.6 g., 20 mmole) is added. The resulting dark mixture is allowed to cool and stand overnight. The precipitate of dye is filtered off and washed with acetonitrile and ether. On recrystallization from acetonitrile, a 25% yield (0.85 g.) of purified dye is obtained with a m.p. of 154°-155° C. dec.

Aufarbeitung

  1. temperatureto cool
  2. filtrationThe precipitate of dye is filtered off
  3. washwashed with acetonitrile and ether
  4. customOn recrystallization from acetonitrile
  5. customa 25% yield (0.85 g.) of purified dye is obtained with a m.p. of 154°-155° C. dec.

Quellen und Nachweise

ORD-Eintrag
ord-33af87ddf59c451298e3aab5131f534e
Quelldatensatz
uspto-grants-1976_10
Patentnummer
US03984248

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