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

HRID 548412

Reaktionsgleichung

Reaktionsgleichung von HRID 548412
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+]>C(O)C>[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-nitro-quinoline-3-carbonitrile and 8.00 g (31.9 mmol) of 3,4-dibromoaniline in 160 mL of ethanol was refluxed under N2 for 5 h. Saturated sodium bicarbonate was added and volatile material was removed. The residue was slurried with hexane, collected, washed with hexane and water and dried. The insoluble material was repeatedly extracted with boiling ethyl acetate and the solution was then filtered through silica gel. The solvent was removed to give 3.80 g of green solid: mass spectrum (electrospray, m/e): M+H 449.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c9ea4910536349a2889684fac04589e6
Quelldatensatz
uspto-grants-2011_05
Patentnummer
USRE042376E1

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