Pyridine → 2-Cyano-4,4'-dinitrobenzanilide

HRID 236991

Reaktionsgleichung

Reaktionsgleichung von HRID 236991
[N+:1]([C:4]1[CH:11]=[C:8](C#N)[C:7]([NH2:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14].[N:25]1C=CC=C[CH:26]=1>>[C:26]([C:23]1[CH:24]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=[CH:18][C:19]=1[C:20]([NH:12][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:8]=1)=[O:21])#[N:25]

Komponenten

4

Edukt 3

HCID 1049PyridineHCID 85024-Nitrobenzoyl chlorideHCID 285322-Amino-5-nitrobenzonitrile

Produkt 1

HCID 196897482-Cyano-4,4'-dinitrobenzanilide

Versuchsvorschrift

To a stirred solution of 16.3 gm. (0.1 mole) of 5-nitroanthranilonitrile in 100 ml. of dry pyridine is added 18.56 gm. (0.1 mole) of p-nitrobenzoyl chloride. The reaction mixture is refluxed for three hours. The pyridine is distilled in vacuo. The oily residue is poured into 600 ml. of water and is distilled in vacuo. The oily residue is poured into 600 ml. of water and the precipitate removed by filtration. The precipitate is boiled with 1500 ml. of ethanol. The insoluble material is removed by filtration. There is obtained 21.57 gm. of yellow solid that melts at 195°-196°.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for three hours
  2. distillationThe pyridine is distilled in vacuo
  3. additionThe oily residue is poured into 600 ml
  4. distillationof water and is distilled in vacuo
  5. additionThe oily residue is poured into 600 ml
  6. customof water and the precipitate removed by filtration
  7. customThe insoluble material is removed by filtration
  8. customThere is obtained 21.57 gm

Quellen und Nachweise

ORD-Eintrag
ord-072bd00c4d364f27ba506dd334e371b4
Quelldatensatz
uspto-grants-1979_06
Patentnummer
US04159341

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