Ethanol → 8-Bromo-2-methylquinoline-4-carboxylic Acid Ethyl Ester
Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[C:7]2[C:13]([OH:15])=[O:14].S(=O)(=O)(O)O.[CH2:21](O)[CH3:22]>>[CH2:21]([O:14][C:13]([C:7]1[C:6]2[C:11](=[C:2]([Br:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=[C:9]([CH3:12])[CH:8]=1)=[O:15])[CH3:22]Komponenten
4
Versuchsvorschrift
A stirred mixture of 8-bromo-2-methylquinoline4-carboxylic acid (7.2 g), ethanol (150 ml) and conc. sulfuric acid (3 ml) was boiled for 6 h. After cooling to room temperature solvent was removed at reduced pressure, the residue treated with water and neutralised with solid potassium carbonate. The neutralised mixture was extracted with ethyl acetate, the extracts dried (MgSO4) and solvent removed at reduced pressure. The residue was column chromatographed (silica gel (30% diethyl ether/60-80 petroleum ether) to give the ester (2.5 g). m/z (API+): 294, 296 (MH+).