O-Toluidine → 3-(3-(Ethoxycarbonyl)propionyl)-8-methoxy-4-((2-methylphenyl)amino)quinoline
反応式
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:22])[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].[NH2:23][C:24]1[C:25]([CH3:30])=[CH:26][CH:27]=[CH:28][CH:29]=1>O1CCCC1>[CH2:20]([O:19][C:17]([CH2:16][CH2:15][C:14]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH3:30])=[CH:10][CH:9]=[CH:8][C:7]=2[O:12][CH3:13])=[O:22])=[O:18])[CH3:21]参加物
4
反応条件
- 温度
- 60 °C
実験手順
In a flame-dried, three-necked round-bottomed reaction flask equipped with reflux condenser, magnetic stirring bar and addition funnel, there were placed 1.72 g (0.00535 mole) of 4-chloro-3-(3-ethoxycarbonylpropionyl)-8-methoxyquinoline (the product of Preparation C) dissolved in 15 mL of dry tetrahydrofuran. Stirring was commenced and the resulting organic solution was then treated dropwise with a solution consisting of 573 mg (0.00535 mole) of o-toluidine (available from the Aldrich Chemical Company, Inc. of Milwaukee, Wis.) dissolved in 15 mL of dry tetrahydrofuran. The resulting reaction mixture was then stirred and heated to 60° C. and thereafter kept at that temperature for a period of approximately 16 hours (i.e., overnight). Upon completion of this step, the final reaction mixture was slowly allowed to cool to ambient temperatures (ca. 20° C.) and the yellow precipitate which resulted was subsequently collected by means of suction filtration and air-dried on the filter funnel to constant weight. Recrystallization of the latter crude salt material from methylene chloride/ethyl acetate/petroleum ether then gave 1.75 g (76%) of pure 3-(3-ethoxycarbonylpropionyl)-8-methoxy-4-(2-methylphenylamino)quinoline as the hydrochloride salt, m.p. 210°-211° C. The pure product was further characterized by means of mass spectrum (MS) analysis and nuclear magnetic resonance (NMR) data, in addition to elemental analysis.