Potassium Carbonate → methyl 2-{4-[N-(6-chloro-2-quinolinyl)-N-methylamino]-phenoxy}propionate

반응식

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[CH3:13])[CH:6]=[CH:5]2.Br[CH:22]([CH3:27])[C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH:22]([CH3:27])[C:23]([O:25][CH3:26])=[O:24])=[CH:16][CH:15]=1)[CH3:13])[CH:6]=[CH:5]2

참가 물질

실험 절차

A mixture of 4-[N-(6-chloro-2-quinolinyl)-N-methylamino]phenol (1.1 g), methyl 2-bromopropionate (1.3 ml), anhydrous potassium carbonate (0.7 g) and acetone (20 ml) was heated under reflux with stirring for a period of 16 hours. The acetone was removed by distillation under reduced pressure and the residue was partitioned between water and chloroform. The chloroform extracts were dried (anhydrous MgSO4) and the solvent was evaporated. The residue was chromatographed over silica gel (40 g) with chloroform elution to give methyl 2-{4-[N-(6-chloro-2-quinolinyl)-N-methylamino]-phenoxy}propionate (1.05 g) as a colourless oil. Proton magnetic resonance spectrum (CDCl3 ; δ ppm); 8.0-6.6 (9H, m, quinoline and phenoxy protons); 4.9 (1H, q, CH--CH3); 3.9 (3H, s, OCH3); 3.6 (3H, s, N--CH3); 1.6 (3H, d, CHCH3).