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CAS No. : | 1762-46-5 | MDL No. : | MFCD11110569 |
Formula : | C16H16N2O4 | Boiling Point : | - |
Linear Structure Formula : | CH3CH2OCOC5H3NC5H3NCOOCH2CH3 | InChI Key : | IUNBUYCOAQHBMC-UHFFFAOYSA-N |
M.W : | 300.31 | Pubchem ID : | 12227215 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
77% | at 0℃; for 24 h; Reflux | Diethyl 2,2'-bipyridine-5,5'-dicarboxylate Procedure: Bipy55'DC (200 mg, 0.82 mmoles) and EtOH (13 mL) were added to a dried flask and stirred on ice. Thionyl chloride (1.3 mL) was added dropwise on ice, after which the flask was fitted with a reflux condenser and heated at reflux. After 24 hr, the reaction was cooled on ice and quenched by the dropwise addition of saturated Na2CO3 (20 mL). The aqueous layer was extracted with CH2Cl2 (4*20 mL) and the combined organics were dried over Na2SO4(s), and concentrated under reduced pressure. The crude product was then purified by chromatography on silica (3percent acetone in 1:1 DCM/hexanes) to afford the title compound (190 mg, 77percent) as a white solid. 1H NMR (500 MHz, CDCl3) δ 9.32 (dd, J=0.5, 2.0 Hz, 1H), 8.59 (dd, J=0.5, 8.5 Hz, 1H), 8.46 (dd, J=2.0, 8.5 Hz, 1H), 4.47 (q, J=7.5 Hz, 2H), 1.46 (t, J=7.5 Hz, 3H); 13C NMR (125 MHz, CDCl3) δ 165.2, 158.3, 150.6, 138.1, 126.6, 121.3, 61.6, 14.3; HRMS (ESI) m/z 301.1193 [calc'd for C16H17N2O4 (M+H)+ 301.1183]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With palladium diacetate; potassium carbonate In N,N-dimethyl-formamide; isopropyl alcohol at 100℃; for 6 h; | General procedure: A 100 mL round bottom flask was equipped with a magnetic stir bar and charged with the appropriate aryl iodide (1 equiv), K2CO3 (1.5 equiv), iPrOH (2 equiv), Pd(OAc)2 (5 mol percent), and a sufficient volume of DMF to make a 0.35 M solution. The reaction mixture was placed under nitrogen and heated to 100 C for 2–5 h until the starting material was consumed as judged by TLC analysis. The reaction mixture was cooled to room temperature and brine (40 mL) was added. The resulting mixture was transferred to a separatory funnel and extracted with EtOAc (3 × 75 mL). The organic layers were combined, washed with brine (1 × 75 mL), dried with Na2SO4, and the solvent was removed in vacuo to afford the crude product as a solid. The crude solid was purified by flash column chromatography or by recrystallization. |