Water → 6-Bromo-2-(2-furanyl)-4-quinolinecarboxylic acid

Participants

Reaction Steps

To a 500 ml three necked round bottom flask was added 5-bromoisatin (20 g) and 2-acetyl-furan (9.7 g) in ethanol (150 ml) followed by NaOH (9.2 g) in one lot and the resulting brown solution was allowed to stir at RT for 5 minutes. To the above reaction mixture was added water (5 ml) at RT and the reaction mixture was heated to reflux for 2 hours. The completion of the reaction was monitored on TLC using MDC:MeOH (9:1) as a mobile phase. After completion of the reaction, the reaction mixture was filtered hot and water (150 ml) was added to filtrate. The filtrate was then acidified with 5N HCl to pH 6.0-6.5 and the precipitate formed was filtered and washed with water (3*50 ml) followed by ethanol (2*10 ml) to yield 6-bromo-2-(furan-2-yl)quinoline-4-carboxylic acid (20 g).

Provenance & Evidence