Uses
5-Fluoro-2-nitrobenzoic acid is used in the production of pharmaceuticals, dye carriers, plasticizers, fragrances and food preservatives, and is also used to improve the performance of alkyd resin coatings.
Chemical Properties
white to light yellow crystal powder
Uses
5-Fluoro-2-nitrobenzoic acid, an
ortho-nitro benzoic acid derivative, can be prepared by the oxidation of 5-fluoro-2-nitrotoluene. It is an intermediate formed during the synthesis of
N1-(2,4-dichlorophenyl)-2-amino-5-fluorobenzamide.
It participates in the synthesis of novel quinazolinones that are potential inhibitors of p38α mitogen-activated protein kinase (MAPK).
General Description
5-Fluoro-2-nitrobenzoic acid, an
ortho-nitro benzoic acid derivative, can be prepared by the oxidation of 5-fluoro-2-nitrotoluene. It is an intermediate formed during the synthesis of
N1-(2,4-dichlorophenyl)-2-amino-5-fluorobenzamide. It participates in the synthesis of novel quinazolinones that are potential inhibitors of p38α mitogen-activated protein kinase (MAPK).
Synthesis
a) General procedure for the synthesis of 5-fluoro-2-nitrobenzoic acid: 3-fluorobenzoic acid (7.9 g, 56 mmol) was dissolved in concentrated sulfuric acid (50 mL), and the solution was cooled to 0 °C. Fuming nitric acid (4.7 g, 67 mmol) was added dropwise with stirring. After the dropwise addition, the reaction mixture was slowly warmed to room temperature and stirring was continued for 1 hour. Upon completion of the reaction, the mixture was carefully poured into water (750 mL) and extracted with ethyl acetate (3 x 100 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 5-fluoro-2-nitrobenzoic acid as a light yellow solid (9.6 g, 52 mmol, 93% yield).1H NMR (300 MHz, d6-DMSO) data for 5-fluoro-2-nitrobenzoic acid: δ 7.66 (m, 1H), 7.74 (m, 1H), 8.17 (m, 1H) ppm.
References
[1] Patent: US5514676, 1996, A
[2] Tetrahedron, 2006, vol. 62, # 31, p. 7284 - 7292
[3] Patent: WO2006/95014, 2006, A1. Location in patent: Page/Page column 41
[4] Patent: WO2004/74218, 2004, A2. Location in patent: Page 106
[5] Patent: US2008/139551, 2008, A1. Location in patent: Page/Page column 43
