2-Iodo-4-nitroaniline

Yellow-red cryst

General procedure: Iodination of phenol (1d) in the presence of Na2SO3 (typical procedure). A 100-mL round-bottom flask was charged with a solution of 3 mmol of phenol in 10 mL of acetic acid, and a solution of KI3 and Na2SO3 (prepared preliminarily by addition of 3 mmol of iodine and 3 mmol of Na2SO3 to a solution of 3 mmol of potassium iodide in 3 mL of water) was added rapidly. At the same time, a solution of 3 mmol of NaIO4 in 5 mL of water was added, and 0.5 mL of sulfuric acid was rapidly added using a pressure-equalizing dropping funnel. The mixture was stirred at 25°C, the progress of the reaction being monitored by TLC. When the reaction was complete, the mixture was poured into ice-cold water, and the solid product was separated by vacuum filtration, washed twice with deionized water, and dried.General procedure: To a stirred solution of the substrate (1 mmol) in CHA solution of 4-nitroaniline (298.2 mg, 2.16 mmol, 1.0 equiv) in CH3CN (3.0 mL) at roomtemperature was sequentially added with NIS (579.1 mg, 2.36 mmol, 1.1 equiv) and TMSCl (27μL, 23.1 mg, 0.21 mmol, 0.1 equiv) and was allowed to stir at room temperature. Uponcompletion, as judged by TLC (approximately 20 min), the reaction mixture was added withwater and the separated aqueous phase was extracted with EtOAc (3x times). The combinedorganic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4 and concentrated underreduced pressure. The crude material was purified by SiO2 column chromatography eluting with50percent EtOAc-hexane to yield 545.6 mg (96percent) of 2-iodo-4-nitroaniline as a yellow crystal.General procedure: To a solution of aromatic compound (10 mmol) in acetonitrile (5 mL) in a 100 mL round-bottomed flask with a magnetic bar was added choline chloride(10 mmol), potassium peroxodisulfate (10 mmol) and iodine (15 mmol). The reaction mixture was stirred for the appropriate time at 65 °C. The progress of the reaction was monitored by TLC. The reaction mixture was poured into aqueous sodium thiosulfate solution (1 mol/L) in order to remove unreacted iodine and extracted with ethyl acetoacetate (10 mL, 3 times). Organic layer is dried over anhydrous sodium sulphate. Evaporation of the solvent under vacuum followed by column chromatography on silica gel gave the corresponding iodinated compounds (Scheme-I).42.7 g (0.309 mol) of 4-nitroaniline were dissolved in the hot state (in the region of 80° C.) in 150 ml of acetic acid. A typical procedure was followed for one-pot synthesis of substituted 2-iodoaniline and 2-iodoacetanilide from substituted aniline. A mixture of 5 g of substituted aniline 1–6 shown inTable 1, granulated iodine (1 mol. equiv.) and copper(II) acetate(1 mol. equiv.) were stirred in 50 mL of glacial acetic for 30 min.The reaction mixture was refluxed for 12 h with constant stirring at 120 C. Then the reaction mixture was allowed to cool at room temperature. The precipitate of copper(I) iodide was removed byfiltration and the filtrate was poured into water and extracted with chloroform (3 50 mL). The combined chloroform extracts were washed with sodium hydrogen carbonate solution, sodium thiosulfate solution, distilled water and dried with anhydrous sodium sulfate.A crude semi-solid mass was obtained after removal of solvent. The crude product was purified by column chromatographyon silica gel using n-hexane/ethyl acetate as eluant (4:1) and compounds 7–24 were isolated.

Molecular Weight:264.02
XLogP3:1.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:263.93957
Monoisotopic Mass:263.93957
Topological Polar Surface Area:71.8
Heavy Atom Count:11
Complexity:159
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes