Methanol → 5-Chloro-6-methoxypyridine-3-carboxylic acid

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Reaction Steps

5,6-Dichloro-nicotinic acid (1.00 g, 5.21 mmol) is added to a solution of Na (252 mg, 10.9 mmol) in methanol (50 mL). The mixture is refluxed overnight before another portion of Na (252 mg, 10.9 mmol) is added. Refluxing is continued for 2 h. The mixture is cooled to rt, diluted with water and concentrated. The remaining solid is dissolved in water and the solution is neutralised by adding 2 N aq. HCl. The resulting suspension is extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered, concentrated and dried to give 5-chloro-6-methoxy-nicotinic acid (976 mg) as a white solid; LC-MS: tR=0.77 min; [M+1]+=189.90; 1H NMR (D6-DMSO): δ 4.03 (s, 3H), 8.22 (d, J=1.8 Hz, 1H), 8.67 (d, J=2.0 Hz, 1H).

Provenance & Evidence