Sodium Hydroxide → 5-Iodo-6-isopropoxynicotinic acid

Participants

Reaction Steps

To a solution of 210 mg (0.63 mmol) of ethyl 5-iodo-6-isopropoxynicotinate (from Step B) in 2.5 mL isopropanol was added 250 μL of 5.0 N NaOH. After stirring at rt for S h, the reaction mixture was partitioned between EtOAc (10 mL) and 1.0 N HCl (10 mL). The organic layer was separated, washed with brine (3×5 mL), dried over MgSO4, and concentrated to give 190 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.44 (d, J=6.4, 6H), 5.44 (m, 1H), 8.66 (d, J=2.1, 1H), 8.83 (d, J=2.1, 1H).

Provenance & Evidence