Chemical Properties
white crystalline powder
Uses
2-Fluorobenzamide can be useful in microwave assisted preparation of oxazole-dehydrozingerone based hybrid molecules as anti-tubercular agents and their docking for Mtb DNA gyrase.
General Description
2-Fluorobenzamide inhibits the activity of poly(ADP-ribose) synthetase
in vitro. It undergoes coupling with anilines in the presence of lithium amides to yield
N-arylanthranilamides.
Synthesis
The general procedure for the synthesis of o-fluorobenzamide from (E)-2-fluorobenzaldehyde oxime was as follows: (E)-2-fluorobenzaldehyde oxime (69.6 mg, 0.5 mmol) and [Cp*Ir(H2O)3][OTf]2 (5.1 mg, 0.0075 mmol) were added sequentially to a 25 mL Schlenk reaction flask. The reaction mixture was stirred at 110 °C for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and the solvent was removed by rotary evaporation. The crude product was purified by column chromatography to give o-fluorobenzamide in 83% yield. The structure of the product was confirmed by nuclear magnetic resonance hydrogen (1H NMR) and carbon (13C NMR) spectra: 1H NMR (400 MHz, DMSO-d6) δ 7.54-7.50 (m, 1H, ArH), 7.29-7.25 (m, 3H, ArH); 13C NMR (100 MHz, DMSO-d6) δ 162.3 (d, JCF = 247.7 Hz), 132.4 (d, JCF = 8.8 Hz), 130.1 (d, JCF = 6.6 Hz), 124.3 (d, JCF = 2.6 Hz), 123.8 (d, JCF = 14.0 Hz), 116.0 (d, JCF = 22.5 Hz).
References
[1] RSC Advances, 2016, vol. 6, # 43, p. 37093 - 37098
[2] Organometallics, 2012, vol. 31, # 17, p. 6482 - 6490
[3] Catalysis Science and Technology, 2014, vol. 4, # 4, p. 988 - 996
[4] Patent: CN104418682, 2016, B. Location in patent: Paragraph 0047-0050
