Hydrogen Bromide → 6-Dimethylamino-4-(beta-bromoethylamino)quinoline

Participants

Reaction Conditions

Reaction Steps

Hydrobromic acid (6.6 ml, 122 mmol) and then sulphuric acid (2.2 ml, 41.4 mmol) are added dropwise to the 6-dimethylamino-4-(β-hydroxyethylamino)quinoline 13 (4.56 g, 19.7 mmol), the reaction medium being refrigerated using a bath of cold water. The reaction medium is then heated at 165° C. for 3 h 30 min and then poured into 71 ml of cold water. The pH is then adjusted by adding NaHCO3 (pH approximately 9) and the medium is then extracted at the reflux of toluene (71 ml) for 15 min. The organic phase is then collected and the product is obtained by crystallization at −18° C. overnight, filtration, and then washing with hexane and drying under vacuum: 3.28 g (yield=57%).

Provenance & Evidence