Sodium Azide → 7-Azido-6-nitro-4-(3,4,5-trimethoxyanilino)-3-quinolinecarbonitrile

HRID 2213734Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2213734
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:14][C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)=[C:7]([C:12]#[N:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:27]([O-:29])=[O:28].[N-:30]=[N+:31]=[N-:32].[Na+]>CS(C)=O>[N:30]([C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:14][C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)=[C:7]([C:12]#[N:13])[CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:27]([O-:29])=[O:28])=[N+:31]=[N-:32]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 21956430HCID 21956430, Verbindung

Produkt 1

HCID 219564987-Azido-6-nitro-4-(3,4,5-trimethoxyanilino)-3-quinolinecarbonitrileAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of 506.1 mg (1.2 mmol) of 7-chloro-6-nitro-4-(3,4,5-trimethoxyanilino)-3-quinolinecarbonitrile and 390.0 mg (6.0 mmol) of sodium azide in 10.0 mL of DMSO is heated at 40–50° C. for 5 hours, and then at room temperature for 15 hours. The mixture is poured into ice water and extracted with ethyl acetate. The organic phase is washed with brine and dried over sodium sulfate. Removal of the solvent yields 493.4 mg (97.7%) of 7-azido-6-nitro-4-(3,4,5-trimethoxyanilino)-3-quinolinecarbonitrile as a yellow solid which is used in the next reaction without further purification.

Aufarbeitung

  1. temperatureis heated at 40–50° C. for 5 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-a5ee36a716dd412380844ada25c01d2b
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105531B2

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