Isatin → 2-(2-Carboxyphenyl)-4-quinolinecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

In 15 ml of water were dissolved 14.7 g (0.1 mol) of isatin and 8 g (0.2 mol) of sodium hydroxide. Then, 16.4 g (0.1 mol of 2-acetylbenzoic acid was added thereto and the resulting mixture was heated at 90° C. under reflux. When the reaction became mild, the mixture was heated at 115° C. for an additional 1 hour. After allowing to cool to room temperature, it was poured into 300 g of water cooled with ice. The aqueous layer was washed with ether and acidified with 2M hydrochloric acid. The precipitate thus formed was collected by filtration to thereby give 9.85 g of 2-(2-carboxyphenyl)-4-quinolinecarboxylic acid. NMR (270 MHz, CD3COCD3): δ 7.70-8.70 (m,9H).

Provenance & Evidence