7477-10-3

2-Chloro-3-nitro-5-pyridinecarboxylic acid is mainly used in organic synthesis and experimental research.

2-Chloro-3-nitro-5-pyridinecarboxylic acid is a heterocyclic organic compound characterized by a pyridine ring substituted with a chlorine atom, a nitro group, and a carboxylic acid functional group. The presence of the chlorine atom at the 6-position and the nitro group at the 5-position contributes to its reactivity and potential applications in various chemical syntheses. The carboxylic acid group at the 3-position enhances its solubility in polar solvents and allows for further functionalization.

General procedure for the synthesis of 6-chloro-5-nitronicotinic acid from 2-chloro-3-nitro-5-methylpyridine: Sodium dichromate (2.5 g) was slowly added to a mixture of 2-chloro-3-nitro-5-methylpyridine (1.0 g, 6.5 mmol) and concentrated sulfuric acid (27 mL). The reaction mixture was stirred at room temperature for 15 hours and then slowly poured into crushed ice to quench the reaction. The mixture was extracted with ethyl acetate (EtOAc). The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 6-chloro-5-nitronicotinic acid (product) as a green solid (1.0 g, 85% yield).1H NMR (300 MHz, DMSO-d6) δ: 13.32 (s, 1H, carboxylate proton), 8.64 (d, J = 2.4Hz, 1H, pyridine ring proton), 8.37 ( d, J = 2.4Hz, 1H, pyridine ring proton).

[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 5, p. 985 - 995
[2] Patent: EP2366691, 2011, A1. Location in patent: Page/Page column 9