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CAS No. : | 1008-89-5 | MDL No. : | MFCD00006280 |
Formula : | C11H9N | Boiling Point : | - |
Linear Structure Formula : | (C6H5)(C5H4N) | InChI Key : | VQGHOUODWALEFC-UHFFFAOYSA-N |
M.W : | 155.20 | Pubchem ID : | 13887 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With oxone; Ru(MesCO2)(4,4'-dibromobipyridine)(p-cymene); trifluoroacetic acid; trifluoroacetic anhydride; In 1,2-dichloro-ethane; at 140℃; for 8h;Sealed tube; Green chemistry; | General procedure: A mixture of 2-arylpyridines (1 eq), Ru(MesCO2)(L) (p-cymene) [L- 2,2?-bypyridine or 4,4?-dibromobipyridine] (5 mol%), TFA: TFAA=0.6 ml:0.4 ml and Oxone (4 eq) was taken in a 30 ml sealed tube. 1 ml of DCE was added and the tube was then placed in an oil bath, stirred, and heated at 140C. The progress of the reaction was checked after every 8 hrs. After complete consumption of starting material the reaction mixture was cooled to room temperature, quenched with brine and extracted with dichloromethane. The combined organic layer was dried with anhydrous Na2SO4, and vacuum evaporated. The crude product was purified over a column of silica gel (eluent: hexane/ethyl acetate) to afford the desired products. |
67% | With water; oxygen;copper diacetate; In acetonitrile; at 130℃; for 36h;Product distribution / selectivity; | EXAMPLE 1; Synthesis of 2-(pyridine-2-yl)phenol (Ib)In a 20 mL tube, 2-phenylpyridine (0.3 mmol, 1 equiv), Cu(OAc)2 (54.6 mg, 0.3 mmol, 1 equiv) and H2O (5.4 muL, 0.3 mmol, 1 equiv) were dissolved in 1 mL of dry MeCN under * oxygen. The tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at 1300C for 36 h. The reaction mixture was diluted with 20 mL of CH2Cl2 and then treated with 10 mL of saturated Na2S aqueous solution. The mixture was filtered through a pad of Celite, and the filtrate was washed twice with brine. The organic layer was dried over Na2SO4 and concentrated under vacuum. After purification by column chromatography on silica gel with a gradient eluent of hexane and ether (Rf = 0.35 in 2:1 hexane: ether), the title product was obtained as a colorless oil (34.4 mg, 67%). 1H NMR (400 MHz, CDCl3) delta 14.39 (s, IH), 8.52 (d, J== 4.8 Hz, IH), 7.93 (d, J= 8.4 Hz, IH), 7.87-7.84 (m, IH), 7.81 (d, J= 8.0 Hz, IH), 7.31 (td, J= 7.6, 1.2 Hz, IH), 7.27-7.24 (m, IH), 7.03 (d, J= 8.0 Hz, IH), 6.92 (td, J = 7.6, 1.2 Hz, IH); 13C NMR (100 MHz5 CDCl3) delta 160.29, 158.10, 146.08, 138.05, 131.77, 126.39, 121.79, 119.31, 119.05, 118.89; IR (thin film) v 2923, 1594, 1477, 1270 cm"1; HRMS (TOF) Calcd for CnH10NO (M+ H) 172.0762, found 172.0768. |
30% | With 18O-labeled water;copper diacetate; In acetonitrile; at 130℃; for 36h;Mechanism; | EXAMPLE 6; Labeling ExperimentIn a 20 mL tube, substrate (0.3 mmol, 1 equiv), Cu(OAc)2 (54.6 mg, 0.3 mmol, 1 equiv) and H218O (5.4 muL, 0.3 mmol, 1 equiv) were dissolved in 1 mL of dry MeCN under N2. The <n="42"/>tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at 130C for 24 h. The reaction mixture was diluted with 20 mL of CH2CI2 and then treated with 10 mL of saturated Na2S aqueous solution. The mixture was filtered through a pad of Celite, and the filtrate was washed twice with brine. The organic layer was dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel (Rf = 0.35, in 2:1 hexane and ether) to give the product in 30% yield. By the analysis of GC-MS, no I8O-labeled hydroxylated product was detected and only hydroxylated product Ib was obtained. |
22% | With water; oxygen;copper (II)-fluoride; In dimethyl sulfoxide; at 130℃; for 24h;Product distribution / selectivity; | Hydroxylation by CuF 2In a 20 mL tube, substrate (0.3 mmol, 1 equiv), CuF2 (30.5 mg, 0.3 mmol, 1 equiv) andH2O (27 muL, 1.5 mmol, 5 equiv) were dissolved in 1 mL of dry DMSO under atmospheric air. The tube was sealed with a Teflon lined cap, and the reaction mixture was stirred at1300C for 24 h. The reaction mixture was diluted with 20 mL of CH2Cl2 and then treated <n="39"/>with 10 mL of saturated Na2S aqueous solution. The mixture was filtered through a pad of Celite, and the filtrate was washed twice with brine. The organic layer was dried over Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel (Rf = 0.35 in 2:1 hexane: ether), Ib was obtained as a colorless oil (11.2 mg, 22%). |
With tert.-butylhydroperoxide; palladium dichloride; In water; chlorobenzene; at 140℃; for 24h;Green chemistry; | To a clean, dry carousel tube, PdCl2 (0.05mmol,8.87mg), 2-phenylpyridine (2mmol,0.286ml), tbutylhydroperoxide (70%solutioninwater, 6mmol, 1.04ml) and chlorobenzene (5mL) were added. The reaction was heated to 140 oC with stirring for 24 h before being cooled to rt. The reaction mixture was filtered through celite and the solvent removed. The crude mixture was then purified by flash column chromatography eluting with dichloromethane to give the phenolic intermediate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.4% | In 1,2-dimethoxyethane; at 198 - 200℃; for 1.1h;Microwave irradiation; Inert atmosphere; | 300 g of 2-phenylpyridinato, 30.1 g of a chlorine-bridged iridium dimer (D-1) and 3 L of special-grade ethylene glycol were placed in a 6 L separable flask, and the flask was set in a cavity-type microwave irradiation apparatus (SMW-124 manufactured by Shikoku Instrumentation CO., Inc.). An argon gas was blown into the reaction solution for 30 minutes, the reaction solution was thereafter irradiated with a microwave (2450 MHz) at 6 kW while the reaction solution was magnetically stirred, the temperature was elevated from room temperature to a boiling state (around 198° C. to 200° C.) in about 6 minutes, and the reaction solution was further irradiated with a microwave at 6 kW for an hour under an argon atmosphere, and reacted at around 198° C. to 200° C. The reaction solution was cooled to room temperature, and thereafter the reaction solution was filtered to obtain a yellow solid. The yellow solid was washed with methanol, pure water and methanol again, thereafter dried in a vacuum, and recrystallized from a mixed solvent of DMF and methanol to obtain a complex of tris-orthometallated iridium (T-1) described in chemical formula (chemical formula 11) (yield amount: 33.5 g; yield: 90.4percent). The product was analyzed by HPLC (Prominence manufactured by Shimadzu Corporation; detected wavelength: 300 nm), and resultantly found to be a mixture of a facial isomer and a meridional isomer at a ratio of 99.2:0.8 (molar ratio). |
85.9% | In a Schlenk's flask equipped with a reflux condenser was placed (1,5-cyclooctadiene)iridium(I) chloride dimer (500 mg, 0. 744 mmol, 1 equivalent) and the interior of the flask was substituted with nitrogen. There were successively added 2-ethoxyethanol (5 mL, s/s=10) and 2-phenylpyridine (468 muL, 3.274 mmol, 4.4 equivalents), and the mixture was stirred in a nitrogen atmosphere under refluxing (135°C) for 3 hours. The resulting yellow suspension was cooled to room temperature, to which was added silver (I) trifluoromethanesulfonate (573 mg, 2.232 mmol, 3.0 equivalents), and further stirred at room temperature for 10 minutes to give a dark brown suspension. There was added an additional amount of 2-ethoxyethanol (7 mL, s/s=14) and then dropwise added 2-phenylpyridine (638 muL, 4.464 mmol, 6.0 equivalents), and the mixture was further stirred under refluxing for 3 hours to give an ocher suspension. The solvent was distilled off from the reaction mixture under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: dichloromethane). The column fractions were condensed, and the resulting yellow solid was recrystallized from hexane/dichloromethane to give 837 mg of the title compound (V-i) as yellow powder in 85.9percent yield. 1H NMR (500MHz CD2Cl2) : delta 6.72-6.81 (m, 6H), 6.85-6.93 (m, 6H), 7.56 (ddd, J=0.8, 1.6, 5.5Hz, 3H), 7.62-7.69 (m, 6H), 7.89-7.94 (m, 3H). | |
83.4% | With silver trifluoromethanesulfonate; In 2-ethoxy-ethanol; at 135℃; for 3h;Heating / reflux; | In a Schlenk's flask were placed Compound (II-i) (Bis(2-phenylpyridinato-N,C2')iridium(III) chloride dimer) produced in Example 1 (200 mg, 0.187 mmol, 1 equivalent) and silver(I) trifluoromethanesulfonate (144 mg, 0. 561 mmol, 3.0 equivalents), and the interior of the flask was substituted with nitrogen. There were added 2-ethoxyethanol (1 ml, s/s=5) and 2-phenylpyridine (163 muL, 1.122 mmol, 6.0 equivalents), and the mixture was stirred under refluxing (135°C) for 3 hours. The resulting ocher suspension was condensed, and the residue was purified by silica gel column chromatography (eluent: dichloromethane). The column fractions were condensed, and recrystallized from hexane/dichloromethane to give 208 mg of the title compound (V-i) as yellow powder in 83.4percent yield. NMR data of the product was identical to that of Example 11. |
78% | Step Two:Added 1200 ml of Ethylene Glycol ether to 3 L of four-neck flask, followed with 18 g of Chlorendic compounds, stirred, Nitrogen gas filled in, then heated and refluxed. When the reflux occurred in the flask, added 12 g of solid sodium carbonate all at once. Dissolved 2-Phenyl Pyridine in 100 ml of Glycerol, and then dripped the mixture in forty minutes by using constant pressure drop funnel. Refluxed with stirring, with sampling interval 1 hour, and 2-3 hours later terminated the reaction. (HPLC: products 95percent-97percent)Cooled the reaction system, added 5.5 L of ethyl acetate, and then rinsed with 4 L.x.3 DI water. Dried the organic phase and concentrated solvent with 200 g of Magnesium Sulfate, and deep yellow solid substances reached. By using Methyl Cyanide, the deep yellow solid substances were recrystallized and 15 g of luminous yellow solid substances with 78percent of yield rate reached.1H-NMR (CDCl3, 400Hz): 7.84 (m, 3H), 7.58 (m, 6H), 7.48 (m, 3H), 6.83 (m, 6H), 6.69 (m, 6H). |