Sodium Bicarbonate → 4-[(3,4-Dibromophenyl)amino]-6-nitro-quinoline-3-carbonitrile

HRID 612262

Reaktionsgleichung

Reaktionsgleichung von HRID 612262
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]#[N:16].[Br:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[Br:25])[NH2:21].C([O-])(O)=O.[Na+]>CCO>[Br:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:22]=[CH:23][C:24]=1[Br:25]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 5219813,4-DibromoanilineHCID 110856904-Chloro-6-nitroquinoline-3-carbonitrile

Produkt 1

HCID 101146524-[(3,4-Dibromophenyl)amino]-6-nitro-quinoline-3-carbonitrileAusbeute 31,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 6.20 g (26.6 mmol) of 4-chloro-6-nitroquinoline-3-carbonitrile and 8.00 g (31.9 mmol) of 3,4-dibromoaniline in 160 mL of EtOH was refluxed under N2 for 5 hr. Satd NaHCO3 was added and volatile material was removed. The residue was slurried with hexane, collected, washed with hexane and H2O and dried. The insoluble material was repeatedly extracted with boiling EtOAc and the solution was then filtered through silica gel. The solvent was removed to give 3.80 g of 4-(3,4-dibromophenylamino)-6-nitroquinoline-3-carbonitrile as a green solid: mass spectrum (electrospray, m/e): M+H 448.9.

Aufarbeitung

  1. temperaturewas refluxed under N2 for 5 hr
  2. customvolatile material was removed
  3. customcollected
  4. washwashed with hexane and H2O
  5. customdried
  6. extractionThe insoluble material was repeatedly extracted with boiling EtOAc
  7. filtrationthe solution was then filtered through silica gel
  8. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-bbc4c360a2594a26ad6379e1c4b0f366
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06002008

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