Sodium → 3-butyryl-4-(2-methylphenylamino)-8-(3-(N-methyl-N-(3-phenylpropyl)amino)propoxy)quinoline

HRID 1090667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1090667
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[OH:24])(=[O:5])[CH2:2][CH2:3][CH3:4].[Na].OC1C=CC2C(=CC=CC=2)N=1.Cl.Cl[CH2:39][CH2:40][CH2:41][N:42]([CH3:52])[CH2:43][CH2:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C(O)C>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[O:24][CH2:39][CH2:40][CH2:41][N:42]([CH3:52])[CH2:43][CH2:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 5360545SodiumHCID 104037323-Butyryl-4-(2-methylphenylamino)8-hydroxyquinolineHCID 199136433-chloro-N-methyl-N-(3-phenylpropyl)-1-propylamine hydrochlorideHCID 178515546HCID 178515546, Verbindung

Produkt 1

HCID 100520313-butyryl-4-(2-methylphenylamino)-8-(3-(N-methyl-N-(3-phenylpropyl)amino)propoxy)quinolineAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

3-Butyryl-4-(2-methylphenylamino)-8-hydroxyquinoline (3.2 g, 10 mmol) was dried by azeotroping with toluene, then dissolved in dry ethanol (20 ml). Sodium (0.23 g, 10 mmol) was dissolved in ethanol (15 ml), and added to the hydroxyquinoline. The resulting solution was evaporated, and the solid redissolved in toluene (50 ml). 3-chloro-N-methyl-N-(3-phenylpropyl)-1-propylamine hydrochloride (1.5 g, 5.7 mmol) was added and the mixture heated at reflux under nitrogen for 3 hours. Evaporation of the solvent, chromatography (silica gel, 0-3% methanolic ammonia in chloroform) and crystallisation from ether gave 3-butyryl-4-(2-methylphenylamino)-8-(3-(N-methyl-N-(3-phenylpropyl)amino)propoxy)quinoline (0.9 g, 18%), m.p. 79°-81°.

Aufarbeitung

  1. customby azeotroping with toluene
  2. dissolutiondissolved in dry ethanol (20 ml)
  3. customThe resulting solution was evaporated
  4. dissolutionthe solid redissolved in toluene (50 ml)
  5. temperaturethe mixture heated
  6. temperatureat reflux under nitrogen for 3 hours
  7. customEvaporation of the solvent, chromatography (silica gel, 0-3% methanolic ammonia in chloroform) and crystallisation from ether

Quellen und Nachweise

ORD-Eintrag
ord-2e6d5430f55f4d2bac17d58f66bb06b3
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05082841

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