Water → 6-Bromoquinoline-2-carboxylic acid
Reaktionsgleichung
S(=O)(=O)(O)[OH:2].[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([C:17](Br)(Br)Br)[CH:11]=[CH:10]2.[OH2:21]>>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([C:17]([OH:2])=[O:21])[CH:11]=[CH:10]2Komponenten
4
Reaktionsbedingungen
- Temperatur
- 150 °C
Versuchsvorschrift
Concentrated sulfuric acid (0.75 L) was added during 15 min to a stirred suspension of 6-bromo-2-(tribromomethyl)quinoline (350 g, 0.76 mol) in water (1.75 L). The resulting suspension was heated at 150° C. (bath temperature) for 5 hr. The mixture was cooled and the precipitate was collected by filtration, washed with water and dried to give 6-bromo-2-quinolinecarboxylic acid as a solid (127.6 g). The filtrate was diluted with water (3 L) and a second crop of the product was obtained (55.7 g, combined yield 183.3 g, 96%). 1H NMR (400 MHz, DMSO-d6): 8.50 (d, J=9 Hz, 1H), 8.38 (d, J=2 Hz, 1H), 8.13 (d, J=9 Hz, 1H), 8.06 (d, J=9 Hz, 1H), 7.96 (m, 1H). ES-LCMS m/z 253 (M+H)+.