5-Chloro-8-hydroxyquinoline → 8-(2-Hydroxyethyl)5-chloroquinoline

反応式

[Cl:1][C:2]1[CH:11]=[CH:10][C:9](O)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C1(=O)O[CH2:16][CH2:15][O:14]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[OH:14][CH2:15][CH2:16][C:9]1[CH:10]=[CH:11][C:2]([Cl:1])=[C:3]2[C:8]=1[N:7]=[CH:6][CH:5]=[CH:4]2

参加物

反応条件

温度: 120 °C

実験手順

A mixture of 5-chloro-8-hydroxyquinoline (1 mmol, 180 mg), ethylene carbonate (2 mmol, 180 mg) and Cs2CO3 (0.6 mmol, 195 mg) in dry DMF (10 mL) was stirred vigorously at 120° C. for 3 h. DMF was evaporated under high-vacuum and the residue was dissolved in water (15 mL), extracted twice with dichloromethane (15 mL), and the residue left after evaporation of dichloromethane was chromatographed over silica gel (eluent: 4:1 hexanes-EtOAc). A biege colored solid was obtained (174 mg, 78%).