Pyridinium chloride → HCID 178486402, Verbindung

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Reaktionsgleichung

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]3[CH:15]=[C:14]([OH:16])[C:13]([O:17][CH3:18])=[CH:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:19]#[N:20].[Cl:21][C:22]1[CH:23]=[C:24]([NH2:35])[CH:25]=[CH:26][C:27]=1[S:28][C:29]1[N:30]([CH3:34])[CH:31]=[CH:32][N:33]=1.Cl.N1C=CC=CC=1>C(OCCO)C.C(=O)([O-])[O-].[Na+].[Na+]>[Cl:21][C:22]1[CH:23]=[C:24]([NH:35][C:2]2[C:11]3[C:6](=[CH:7][C:8]4[CH:15]=[C:14]([OH:16])[C:13]([O:17][CH3:18])=[CH:12][C:9]=4[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:19]#[N:20])[CH:25]=[CH:26][C:27]=1[S:28][C:29]1[N:30]([CH3:34])[CH:31]=[CH:32][N:33]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A mixture of 1.0 g (3.53 mmol) of 4-chloro-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile, 0.93 g (3.88 mmol) of 3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamine and 0.41 g (3.52 mmol) of pyridine hydrochloride in 20 mL of 2-ethoxyethanol is heated at 120° C. for 2 hours, then cooled to room temperature. The product mixture is diluted with a saturated solution of sodium carbonate, stirred for 15 minutes and the solid is collected by filtration. The solid is washed with water and dried in vacuo. The crude product is purified by silica gel chromatography, utilizing a 95:5 to 9:1 gradient of methylene chloride/methanol to give 1.13 g of 4-[3-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamino]-8-hydroxy-7-methoxybenzo[g]quinoline-3-carbonitrile as a yellow solid, mp>300° C.

Aufarbeitung

temperaturecooled to room temperature
filtrationthe solid is collected by filtration
washThe solid is washed with water
customdried in vacuo
customThe crude product is purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag: ord-59885a8480a1487a90ba476943dafbc9
Quelldatensatz: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07365197B2

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