3-Bromoaniline → 8-(3-Bromo-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrile

HRID 2213736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2213736
Cl[C:2]1[C:11]2[CH:10]=[C:9]3[N:12]=[CH:13][N:14]=[C:8]3[CH2:7][C:6]=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][CH:24]=1)[NH2:21].Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(OCCO)C>[Br:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[C:11]3[CH:10]=[C:9]4[N:12]=[CH:13][N:14]=[C:8]4[CH2:7][C:6]=3[N:5]=[CH:4][C:3]=2[C:15]#[N:16])[CH:22]=[CH:23][CH:24]=1

Komponenten

6

Edukt 4

HCID 115623-BromoanilineHCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 693728438-Chloroimidazo[4,5-g]quinoline-7-carbonitrile

Produkt 1

HCID 693732468-(3-Bromo-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrileAusbeute 63,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8076Glycol monoethyl etherLösungsmittel

Versuchsvorschrift

A mixture of 0.2 g (0.87 mmol) of 8-chloroimidazo[4,5-g]quinoline-7-carbonitrile, 0.12 mL (1.1 mmol) of 3-bromoaniline, and 0.1 g (0.87 mmol) of pyridine hydrochloride in 5.0 mL of 2-ethoxyethanol is heated at reflux temperature for 45 minutes, then cooled to room temperature. The product mixture is poured into a saturated solution of sodium bicarbonate and stirred for 0.5 hour. The solid is collected by filtration, washed with water and dried. The solid is purified by silica gel chromatography, utilizing a gradient of methylene chloride/methanol (98:2 to 93:7) to yield 0.20 g of 8-(3-bromo-phenylamino)imidazo[4,5-g]quinoline-7-carbonitrile as pink solid, mp 286–288° C.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux temperature for 45 minutes
  3. filtrationThe solid is collected by filtration
  4. washwashed with water
  5. customdried
  6. customThe solid is purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2241d8b284ce4a23b5d2bd3b7668e53b
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105531B2

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