Hydrochloric Acid → 5-Chloro-6-isopropoxynicotinic acid

Participants

Reaction Conditions

Reaction Steps

5,6-Dichloronicotinic acid (1.95 g, 10 mmol) is added to a solution of KOtBu (2.28 g, 20 mmol) in isopropanol (20 mL). The mixture is heated at 80° C. for 15 h. The mixture is diluted with water (60 mL) and acidified with 1M aq. HCl. The aq. solution is extracted with ether (5×50 mL) and the combined org. extracts are dried (Na2SO4), filtered and evaporated to provide 5-chloro-6-isopropoxy-nicotinic acid; 1H NMR (d6-DMSO) δ 1.38 (d, J=6.2 Hz, 7H), 5.44 (hept, J=6.2 Hz, 1H), 8.18 (d, J=2.1 Hz, 1H), 8.65 (d, J=2.1 Hz, 1H)

Provenance & Evidence