HCID 20183595, Verbindung → HCID 20183608, Verbindung

HRID 255560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 255560
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[CH:14][C:13]=2[N+:22]([O-])=O)=[CH:5][CH:4]=1.[H][H]>C1(C)C=CC=CC=1.[Pt]>[NH2:22][C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:12]=1[NH:11][CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2

Komponenten

5

Edukt 2

HCID 20183595HCID 20183595, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 20183608HCID 20183608, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23939PlatinumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Using the method of Example 26, 20.4 g (0.063 mole) of 4-[2-(4-methoxyphenyl)ethylamino]-3-nitroquinoline was reduced by hydrogen in 300 ml of toluene with 5% platinum on charcoal. The solvent was then evaporated to provide a residue of 3-amino-4-[2-(4-methoxyphenyl)ethylamino]quinoline. To this residue was added 28 g (0.19 mole) of triethyl orthoformate and the mixture was heated at about 125° C. for two hours. To this mixture was added about 100 ml of aqueous hydrochloric acid and the mixture was heated on a steam bath for thirty minutes. After cooling, the precipitate was separated by filtration, washed sequentially with isopropanol and diethyl ether, and dried. To the solid was added water and ammonium hydroxide, after which the mixture was cooled and the solid was separated by filtration. A portion (3.5 g) of the solid was dissolved in isopropanol, and acidified with hydrochloric acid. The solid was separated by filtration, washed with isopropanol and dried to provide 1-[2-(4-methoxyphenyl)ethyl]-1H-imidazo[4,5-c]quinoline hydrochloride hydrate, m.p. 209°-213° C. Analysis: Calculated for C19H17N3O.HCl.1/3H2O: %C, 66.0; %H, 5.4; %N, 12.2; Found: %C, 66.1; %H, 5.3; %N, 12.3.

Aufarbeitung

  1. customThe solvent was then evaporated

Quellen und Nachweise

ORD-Eintrag
ord-e93a0b0071c944ac9058d34736026049
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04698348

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