Potassium Carbonate → Ethyl 4-(2-oxopyridin-1(2H)-yl)benzoate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A mixture of 4-bromobenzoic acid ethyl ester (4.58 g, 20.00 mmol), 2-hydroxypyridine (0.95 g, 10.00 mmol), potassium carbonate (1.39 g, 10.00 mmol), and CuI (0.095 g, 0.50 mmol) was stirred at 120° C. for 6 h under a nitrogen atmosphere. The diluted aqueous ammonia (50 mL) was added, and the solution was extracted with ethyl acetate (3×50 mL). The organic extracts were dried over anhydrous sodium sulfate, filtered. The solvent was removed in vacuo to afford ethyl 4-(2-oxopyridin-1(2H)-yl)benzoate in 86% yield (2.10 g); NMR (CDCl3, 300 MHz) δ 8.15 (d, J=8.5 Hz, 2H), 7.46 (d, J=8.5 Hz, 2H), 7.39 (ddd, J=2.0, 6.6, 9.0 Hz, 1H), 7.31 (dd, J=2.0, 6.6 Hz, 1H), 6.65 (d, J=9.0 Hz, 1H), 6.26 (dt, J=1.1, 6.6 Hz, 1H), 4.38 (q, J=7.1 Hz, 2H), 1.39 (t, J=7.1 Hz, 3H).

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