4-(1H-Imidazol-1-yl)aniline

White powder

General procedure: For the catalysis reaction, the catalyst C1 (12 mg, 0.01 mmol), imidazole (1.0 mmol), aryl halide(1.0 mmol), NaOH (80 mg, 2.0 mmol), and dimethylsulfoxide (DMSO, 5 mL) were taken in a sealed tube. The reaction mixture was stirred at 100 °C for 4 h and then cooled to room temperature. After adding 5 mL of H2O, the solution was extracted with ethyl acetate. The organic layer was then dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure.The N-arylated product was finally obtained by columnchromatography on silica gel.General procedure: A mixture of aryl iodide (1.0 mmol), Het-NH (1.2 mmol), KOH (2 mmol), nanomagnetic FeGeneral procedure: A mixture of aryl halide (1.0 mmol), Het-NH (1.2mmol) or amine (4 mmol), KOH (2 mmol), CuGeneral procedure: Arylhalide (1.0 mM), nitrogen-containing heterocycle (1.2 mM), KOH (2 mM), and the catalyst (0.75 Mpercent) were stirred in dimethyl sulfoxide (DMSO) (4 mL) at 110 °C for 10 h. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL) and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane/ethyl acetate(70 : 30) as eluent to afford the desired product. The products have been characterized by 1H NMR spectroscopy.General procedure: NH-containing heterocycle (1.4 mmol) and DMF (2.0 mL) were added to a mixture of CuCl (15.0 molpercent) and ligand 1 (20.0 molpercent) in DMF (2.0 mL), aryl iodide (1.0 mmol), NaOH (2.0 mmol). The mixture was vigorously stirred at 120 °C for 14 h under a dry nitrogen atmosphere. After completion of the reaction (as monitored by TLC), H2O was added and the organic layer was extracted with EtOAc, washed with brine and dried over MgSO4. The solution was filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography. The purity of the compounds was checked by 1H NMR and yields are based on aryl iodide. All the products are known and the spectroscopic data (FT‑IR and NMR) and melting points were consistent with those reported in the literature.General procedure: Arylhalide (1.0 mM), nitrogen-containing heterocycle (1.2 mM), KOH (2 mM), and the catalyst (0.75 Mpercent) were stirred in dimethyl sulfoxide (DMSO) (4 mL) at 110 °C for 10 h. After completion of the reaction, the mixture was cooled to room temperature, diluted with ethyl acetate (10 mL) and filtered. The filtrate was concentrated and the residue was purified by column chromatography on silica gel using hexane/ethyl acetate(70 : 30) as eluent to afford the desired product. The products have been characterized by 1H NMR spectroscopy.General procedure: To a solution of 1-(substituted) 4-nitrobenzene IVa, b, e, f(0.01 mol) in NH4OH (20 mL, 30percent), a solution of sodium dithionite(7 g, 0.04 mol) in water (30 mL) was quickly added, the reactionmixture was refluxed for 15 min. After cooling, the crude productwas filtered, washed and crystallized from methylene chloride toyield target compounds Va, b, e, f. 4-(1H-imidazol-1-yl) aniline Va b 2. General procedure: The optimum reaction conditions were as follows: sodium hydroxide as base (2mmol), dimethyl sulfoxide as solvent (3mL), reaction temperature of 100 , catalyst such as methylene bridged 1, 8-naphthyridine copper () The amount of the complex was 0.01 mmol, and the catalytic expansion experiments were carried out with different substituted aryl bromides and iodide substrates. The results are shown in Table 2.The catalyst system is capable of tolerating a C-N coupling reaction of various functionalized aryl halides, including nitrile, nitro, acetyl and ether groups, wherein the catalytic yield of iodide is between 91% and 99 %between.In addition, when the catalytic reaction is highly selective and the substrate is a hydroxyl group or an amino-substituted aryl bromide, the formation of the diaryl ether compound and the diphenylamine compound can be avoided.Reaction conditions: aryl halide (1.0 mmol), imidazole (1.0 mmol), sodium hydroxide (2.0 mmol), complex (0.01 mmol), dimethyl sulfoxide (3 mL), 100 C air atmosphere, B. Isolated yield; c.2-bromopyridine aryl halide.

Molecular Weight:159.19
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:159.079647300
Monoisotopic Mass:159.079647300
Topological Polar Surface Area:43.8
Heavy Atom Count:12
Complexity:141
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes