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CAS No. : | 612-24-8 | MDL No. : | MFCD00007044 |
Formula : | C7H4N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SWBDKCMOLSUXRH-UHFFFAOYSA-N |
M.W : | 148.12 | Pubchem ID : | 11922 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P271 | UN#: | N/A |
Hazard Statements: | H302+H332 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
76% | With C29H26FeN3Pd(1+)*Cl(1-); oxygen; caesium carbonate; In 1,4-dioxane; dimethyl sulfoxide; at 100℃; for 24h; | General procedure: A reaction vessel was charged with a mixture of phenylboronic acid (1.5mmol), Cs2CO3 (1.0mmol), catalyst Ic (1mol%) in dioxane/DMSO (1:1) (2.0mL), and stirred for about 20min under air. Then 4-nitrobenzaldehyde (0.5mmol) was then added. The mixture was heated to 100C and incubated in an oil bath at 100C for 24h under air. After the reaction was complete, the solvent was evaporated under reduced pressure. The product 3aa was obtained by purifying on preparative TLC, eluting with ethyl acetate/petroleum ether, and the yield was calculated based on the 4-nitrobenzaldehyde (the purified products were identified by NMR spectra and comparison of the melting points with the literature data). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.1% | With p-nitrobenzenesulfonic acid; cis-dichlorobis(triphenylphosphine)molybdenum; 1-ethyl-3-methylimidazolium tetrafluoroborate; bis-[(trifluoroacetoxy)iodo]benzene; 4,4'-di-tert-butyl-2,2'-bipyridine; In N,N-dimethyl-formamide; at 85℃; for 11h;Inert atmosphere; | At room temperature, In the appropriate amount of the organic solvent (A mixture of N, N-dimethylformamide (DMF) and 1-ethylethyl ether-3- in a mass ratio of 5: 1, 100 mmol of the compound of formula (I), 70 mmol of the compound of the formula (II), 4 mmol of catalyst cis-dichlorobis (triphenylphosphine) molybdenum,12 mmol of organic ligand L1,140 mmol of oxidant bis(trifluoroacetate) iodobenzene and 7 mmol of auxiliary p-nitrobenzene sulfonic acid, then purged with nitrogen, until the reaction atmosphere is a nitrogen atmosphere, and stirred heated to 85 C, the reaction was stirred at this temperature for 11 hours;After completion of the reaction, the reaction system was cooled to room temperature, pH adjusted to neutral, and then washed thoroughly with saturated saline, the mixture was further extracted with ethyl acetate for 2-3 times, organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, resulting residue was subjected to silica gel column chromatography, an equal volume ratio of acetone and petroleum ether mixture was rinsed, Thus, the compound of the above formula (III) was obtained in a yield of 96.1%. |
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