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CAS No. : | 2631-77-8 | MDL No. : | MFCD00003321 |
Formula : | C7H4I2O2 | Boiling Point : | - |
Linear Structure Formula : | C6H2I2(OH)CHO | InChI Key : | MYWSBJKVOUZCIA-UHFFFAOYSA-N |
M.W : | 373.91 | Pubchem ID : | 75829 |
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 |
---|---|---|
With piperidine; In ethanol; | General procedure: 3-Carbonyl coumarins were obtained by Knoevenagel cyclization between substituted salicylaldehydes (1 mmol) and methyl acetoacetate (1 mmol) or ethyl benzoylacetate (1 mmol) in ethanol (25 mL) with catalytic amounts of piperidine. The ethyl ester of coumarin-3-carboxylic acid was prepared by Knoevenagel reaction between diethyl malonate (1 mmol) and the appropriate salicylaldehyde (1 mmol) with catalytic amounts of piperidine in ethanol (50 mL). Then, if there was an hydroxyl group at position 7, etherification was performed by adding a suitable benzyl bromide (1 mmol) or cycloheptyl bromide (1 mmol), and potassium carbonate (1 mmol) in anhydrous acetone (100 mL), using N,N'-dicyclohexyl-18-crown-6-ether (1 mmol) as a chelating agent. Final products were purified by chromatography. Ethyl ester derivatives (1 mmol) were dissolved and stirred at room temperature in a solution of LiOH.H2O (6 mmol) in H2O/MeOH (1:5, v/v; 50 mL); then HCl 3 N (50 mL) was added. The suspension was filtered and the solid was dried under vacuum. 3-Carboxyhydrazido derivatives were obtained by dissolving at reflux 3-coumarin carboxylic acid (1 mmol) in thionyl chloride (20 mL). After solvent evaporation under vacuum, the reactive acyl chloride (1 mmol) was reacted with a suitable hydrazine hydrochloride (2 mmol) in the presence of sodium acetate (2 mmol) in H2O/CH3CN (1/4, v/v). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With sodium periodate; sulfuric acid; iodine; potassium iodide; sodium sulfite; In water; acetic acid; at 25℃; for 3h; | 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 25C, 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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperidine; In ethanol; | General procedure: 3-Carbonyl coumarins were obtained by Knoevenagel cyclization between substituted salicylaldehydes (1 mmol) and methyl acetoacetate (1 mmol) or ethyl benzoylacetate (1 mmol) in ethanol (25 mL) with catalytic amounts of piperidine. The ethyl ester of coumarin-3-carboxylic acid was prepared by Knoevenagel reaction between diethyl malonate (1 mmol) and the appropriate salicylaldehyde (1 mmol) with catalytic amounts of piperidine in ethanol (50 mL). Then, if there was an hydroxyl group at position 7, etherification was performed by adding a suitable benzyl bromide (1 mmol) or cycloheptyl bromide (1 mmol), and potassium carbonate (1 mmol) in anhydrous acetone (100 mL), using N,N'-dicyclohexyl-18-crown-6-ether (1 mmol) as a chelating agent. Final products were purified by chromatography. Ethyl ester derivatives (1 mmol) were dissolved and stirred at room temperature in a solution of LiOH.H2O (6 mmol) in H2O/MeOH (1:5, v/v; 50 mL); then HCl 3 N (50 mL) was added. The suspension was filtered and the solid was dried under vacuum. 3-Carboxyhydrazido derivatives were obtained by dissolving at reflux 3-coumarin carboxylic acid (1 mmol) in thionyl chloride (20 mL). After solvent evaporation under vacuum, the reactive acyl chloride (1 mmol) was reacted with a suitable hydrazine hydrochloride (2 mmol) in the presence of sodium acetate (2 mmol) in H2O/CH3CN (1/4, v/v). |
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