Oxalyl chloride → 2-[4-(6,7-Dimethoxyquinolin-4-yloxy)phenyl]acetyl chloride

Participants

Reaction Steps

Oxalyl chloride (0.5 ml) was added dropwise to a stirred suspension of 2-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]acetic acid (0.2 g) in chloroform (5 ml) at ambient temperature under argon. The resultant mixture was heated to reflux for 30 minutes. The mixture was evaporated to leave 2-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]acetyl chloride as a solid. Chloroform (5 ml) and 5-amino-3-methyl-1,2,4 oxadiazole (0.099 g) were added in turn. Pyridine (0.286 ml) was added and the reaction mixture was stirred at ambient temperature for 16 hours. The solvent was evaporated and the residue was purified by preparative HPLC using a Waters ‘Xterra’ reversed-phase column (5 microns silica, 30 mm diameter, 250 mm length) that was eluted with decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. There was thus obtained the title compound (0.053 g); 1H NMR: (DMSOd6) 2.26 (s, 3H), 3.86 (s, 2H), 3.92 (s, 3H), 3.95 (s, 3H), 6.46 (d, 1H), 7.24 (d, 2H), 7.4 (s, 1H), 7.44 (d, 2H), 7.49 (s, 1H), 8.48 (d, 1H), 11.27 (br s, 1H); Mass Spectrum: M+H+ 421.

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