1-Propanol → HCID 19967129, Verbindung
Reaktionsgleichung
[Na].Cl[C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[CH:16]3)[CH:9]=2)[N:4]=1.[CH2:20]([OH:23])[CH2:21][CH3:22]>>[N:15]1([CH2:14][C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[N:4]=[C:3]([O:23][CH2:20][CH2:21][CH3:22])[CH:12]=[C:11]3[CH3:13])[CH:19]=[CH:18][N:17]=[CH:16]1Komponenten
4
Versuchsvorschrift
To a stirred solution of 2 parts of sodium in 24 parts of 1-propanol was added a solution of 5.2 parts of 2-chloro-6-(1H-imidazol-1-ylmethyl)-4-methylquinoline in 16 parts of 1-propanol at room temperature under nitrogen atmosphere. After stirring for 2 hours at reflux temperature, the mixture was evaporated. The residue was taken up in a potassium carbonate solution and the product was extracted with ethyl acetate. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanone. The product was filtered off and dried, yielding 1.8 parts (31.9%) of 6-(1H-imidazol-1-ylmethyl)-4-methyl-2-propoxyquinoline; mp. 137.9° C. (compound 25).