N-(4-bromophenyl)-3-phenylpropanamide Chemical Properties

Boiling point:

473.2±38.0 °C(Predicted)

Density 

1.408±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Most solvents

form 

Solid

pka

13.88±0.70(Predicted)

color 

White

InChI

InChI=1S/C15H14BrNO/c16-13-7-9-14(10-8-13)17-15(18)11-6-12-4-2-1-3-5-12/h1-5,7-10H,6,11H2,(H,17,18)

InChIKey

HGPWLPIFXDCULJ-UHFFFAOYSA-N

SMILES

C1(CCC(NC2=CC=C(Br)C=C2)=O)=CC=CC=C1

N-(4-bromophenyl)-3-phenylpropanamide Usage And Synthesis

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

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