反应详情

Methyl 2-Benzoylnicotinate (2.41 g., 10 mmoles) was dissolved in 250 ml ammonium hydroxide. To this solution was carefully added a catalytic amount of copper (II) sulfate (approx. 100 mg) and zinc powder (7.0 g., 100 mmoles). The mixture was refluxed for 6 days and allowed to cool. The mixture was filtered (pad of celite), acidified to pH 5 with 1N HCl, exhaustively extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered, concentrated under vacuum, and purified by column chromatography to give 0.70 grams (33% yield) of 2-benzylnicotinic acid as a white solid. Characteristic analytical data are as follows: mp 180°-182.5° C.; TLC in 20:1.8:0.2 (EtOAc/MeOH/HOAc); 1H NMR (DMSO-d6, 300 MHz) δ4.50 (s, 2H), 7.12-7.48 (m, 5H), 8.18 (dd, 1H, J=8.0, 1.6 Hz), 8.63 (dd, 1H, J=4.8, 1.5 Hz); 13C NMR (75 MHz, DMSO-d6) δ167.84, 160.17, 151.55, 139.85, 138.38, 128.75, 128.04, 126.37, 125.79, 121.57, 41.35, 39.76; mass spectrum (EI) , m/e 213.

1. temperatureThe mixture was refluxed for 6 days
2. temperatureto cool
3. filtrationThe mixture was filtered (pad of celite)
4. extractionexhaustively extracted with ethyl acetate
5. washwashed with brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under vacuum
9. custompurified by column chromatography