Tetrahydrofuran → HCID 178431739, compound

Participants

Reaction Steps

Potassium hydroxide (1N, 100.0 ml) is added to a mixture of 5-fluoroisatin acetamide (IV, 8.44 g) and THF (33 ml). The mixture is heated at reflux for 1 hr, allowing the THF to distill off. The mixture is then cooled to 5° and is extracted with methylene chloride (3×50 ml). The basic layer is neutralized with hydrochloric acid (4N, 16.3 ml) and the resulting solids collected and washed with water (200 ml) and methylene chloride (100 ml) to give 6-fluoro-2-hydroxyquinoline-4-carboxylic acid (V), mp >293°; IR (mineral oil) 1714, 1648, 1623, 1508, 1436, 1261, 1255, 1244, 1234 and 1222 cm-1 ; NMR (d6 -DMSO) 12.20, 8.04, 7.35-7.60 and 7.00 δ; MS (El, m/e) 207, 162, 135 and 107.

Provenance & Evidence