Dichloromethane → 8-Fluoro-2-methoxyquinoline-4-carboxylic Acid Methyl Ester

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Reaction Steps

8-Fluoro-2-chloroquinoline-4-carboxylic acid (0.986 g) suspended in dichloromethane (50 ml) was treated with dimethylformamide (3 drops) and oxalyl chloride (0.76 ml) and the mixture stirred for 2 h. Solvent was removed at reduced pressure. The residue was dissolved in methanol (50 ml) containing sodium methoxide (0.54 g) and stirred for 16 h. The solvent was removed at reduced pressure and the residue triturated with water. The precipitate was collected by filtration and column chromatographed (silica gel, 10→50% ethyl acetate/hexane) to give the title compound (0.184 g) as a colourless solid. m/z (API+): 236 (MH+). 1H NMR (CDCl3) δ: 4.02 (3H, s), 4.14 (3H, s), 7.36-7.41 (2H, m), 7.49 (1H, s), 8.37 -8.41 (1H, m).

Provenance & Evidence