Methyl 2-Benzoylnicotinate → 2-Benzylnicotinic acid

Reaction equation

[C:1]([C:9]1[N:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13]C)=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[OH-].[NH4+].S([O-])([O-])(=O)=O.[Cu+2].[Zn]>[CH2:1]([C:9]1[N:18]=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Procedure

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.