3-Bromoquinolin-8-amine

Uses

3-Bromoquinolin-8-amine acts as a reagent for the synthesis and structure activity relationship of 3-(arylsulfonyl)-8-(piperidin-4-yl amino)quinoline derivatives as 5-HT6 receptor antagonists for the treatment of Alzheimer''s disease and Schizophrenia. Also acts as a reagent for the synthesis of certain 8-aminoquinolines and antimalarias.

Synthesis

General procedure for the synthesis of 3-bromoquinolin-8-amine from 3-bromo-8-nitroquinoline: to a solution of 3-bromo-8-nitroquinoline (22.00 g, 86.94 mmol) obtained from method 1 in ethanol (1100 ml) was added sequentially water (66 ml), concentrated hydrochloric acid (66 ml), and iron powder (24.28 g, 434.8 mmol), the reaction was at room temperature Carried out. The reaction mixture was refluxed for 1 h and cooled to room temperature and the insoluble material was filtered through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure and 10% sodium bicarbonate solution (700 ml) and ethyl acetate (500 ml) were added to the resulting residue and stirred for 30 minutes. The organic layer was again separated by filtration through a diatomaceous earth pad, washed with brine, dried over magnesium sulfate and decolorized with activated carbon. Finally, the solvent was concentrated under reduced pressure to give 3-bromoquinolin-8-amine (18.11 g, 81.19 mmol, 93.4% yield) as light yellow crystals.

References

[1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 34, p. 8092 - 8100
[2] Patent: EP1375486, 2004, A1. Location in patent: Page 114; 115
[3] Monatshefte fuer Chemie, 1991, vol. 122, # 11, p. 935 - 942
[4] Patent: US2017/29452, 2017, A1. Location in patent: Paragraph 0093-0095
[5] Asian Journal of Chemistry, 2014, vol. 26, # 13, p. 3779 - 3784