[H][H].Cl[C:4]1[CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=[C:6]([CH3:13])[N:5]=1.C(N(CC)CC)C>[Pd].C(O)C>[CH3:13][C:6]1[N:5]=[CH:4][CH:9]=[C:8]([C:10]([OH:12])=[O:11])[CH:7]=1A hydrogen filled balloon was attached to a flask containing 2-chloro-6-methylpyridine-4-carboxylic acid (2 g, 12.0 mmol), palladium 10 wt. % on activated carbon (0.5 g), triethyl amine (4.8 ml) and ethanol (24 ml) and then stirred overnight at room temperature. The is reaction mixture was filtered through celite, washed with methanol and concentrated. The residue was titurated with dichloromethane and then filtered to afford 6-methylpyridine-4-carboxylic acid as a white solid; 1.05 g (66%). 1H NMR (MeOD) δ (ppm): 8.62 (d, 1H), 7.68 (s, 1H), 7.60 (d, 1H), 2.55 (s, 3H).
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