N-(4-bromophenyl)-3-phenylpropanamide

Chemical Properties

N-(4-bromophenyl)-3-phenylpropanamide is White Solid

Uses

N-(4-bromophenyl)-3-phenylpropanamide is a reactant used in the preparation of quinoline derivatives as antitubercular agent and antibacterial agents.

Synthesis

To a solution of 4-bromoaniline (40 g, 0.232 mol) and triethylamine (32 mL) in dichloromethane (200 mL) was slowly added hydrocinnamoyl chloride (37.5 g, 0.223 mol) dropwise at 0 °C. After the dropwise addition was completed, the reaction mixture was stirred at room temperature overnight. After completion of the reaction, the mixture was poured into water and 10% hydrochloric acid solution was added. The white solid slurry formed was stirred for 1 hour under cooling in an ice bath. The solid product was separated by filtration, washed with ether and dried in air to afford N-(4-bromophenyl)-3-phenylpropanamide (62 g, 92% yield).

References

[1] ChemMedChem, 2017, vol. 12, # 2, p. 106 - 119
[2] Chinese Chemical Letters, 2015, vol. 26, # 6, p. 790 - 792
[3] Patent: WO2005/70430, 2005, A1. Location in patent: Page/Page column 34
[4] Patent: WO2007/14885, 2007, A1. Location in patent: Page/Page column 31
[5] Patent: WO2007/14940, 2007, A2. Location in patent: Page/Page column 40-41