Sodium Hydroxide → 5-Cyano-6-ethoxynicotinic acid

Participants

Reaction Steps

To a solution of 498 mg (1.82 mmol) of methyl 5-cyano-6-(2,2,2-trifluoro-1-methylethoxy)nicotinate (from CARBOXYLIC ACID 20, Step C) in 10 mL of EtOH was added 1.8 mL of 5.0 N NaOH. After stirring at rt overnight, the mixture was acidified using Dowex H cation exchange resin until pH=3. The resin was filtered off and the filtrate was concentrated to give 160 mg of the title compound: 1H NMR (500 MHz, CD3OD) δ 1.37 (t, J=7.1, 3H), 4.50 (d, J=7.1, 2H), 8.43 (d, J=2.1, 1H), 8.85 (d, J=2.3, 1H).

Provenance & Evidence