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CAS No. : | 3290-99-1 | MDL No. : | MFCD00017073 |
Formula : | C8H10N2O2 | Boiling Point : | - |
Linear Structure Formula : | H2NNHC(O)C6H4OCH3 | InChI Key : | REKQLYUAUXYJSZ-UHFFFAOYSA-N |
M.W : | 166.18 | Pubchem ID : | 76792 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
96% | With sulfuric acid; acetic acid; In methanol; water; for 1h;Reflux; | General procedure: Compounds of series I were synthesized by refluxing <strong>[92-55-7]5-nitro-2-furaldehyde diacetate</strong> 98% (5 mmol) and benzhydrazides (3) (5 mmol) in water, sulphuric acid, acetic acid, and methanol (8:7:8:20 v/v) for 1 h. After cooling, the mixture was poured into cold water to precipitate the azomethine derivatives 20(see structural elucidation of the compounds of series I in Supplementary data, p. S2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 80℃; for 3h; | General procedure: 8-Methoxyquinoline-2-carbaldehyde (25, 0.534 mmol) was refluxedwith various substituted acylhydrazines (0.587 mmol, 1.1 eq) in ethanol(5-10 mL) to get acyl hydrazides of 8-hydroxyquinoline. After completionof reaction, quinoline acyl hydrazides were found as precipitateson cooling to -15 C. Precipitates were washed with coldethanol and dried under vacuum. These acyl hydrazides were used directlyfor one pot synthesis of 2,5-disubstituted-1,3,4-oxadiazole usingiodine/K2CO3 catalysed oxidative cyclization. To the acyl hydrazides(1.0 eq) in DMSO (5-10 mL), K2CO3 (3.0 eq) and iodine (1.2 eq) wereadded in sequence and refluxed at 110 C. After the completion, thereaction mixture was cooled and saturated solution of sodium thiosulfatewas added. The precipitates were collected and dried under highvacuum to get the respective compounds (33-50). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | In N,N-dimethyl-formamide; for 2h;Reflux; | The aroylhydrazone H2DSMB was prepared by refluxingequimolar N,N-dimethylformamide solutions of 4-methoxybenzhydrazide(0.166 g, 1 mmol) and 3,5-diiodosalicyaldehyde(0.374 g, 1 mmol) for 2 h. The resulting solution was allowed toevaporate at room temperature. Single crystals suitable for X-rayanalysis were obtained within a period of 2-3 days. The productobtained was filtered and dried.Yield: 0.4332 g (83%) Color: Yellow. Anal. Calc. for C15H12I2N2O3(M.W.: 522.07 g mol1): C, 34.51; H, 2.32; N, 5.37. Found: C, 34.09;H, 1.96; N, 5.11%. |
In methanol; for 2h;Heating; | General procedure: Briefly, 4-substituted benzohydrazides (1 mmol) were treated with 2- or 4-hydroxy-3,5-diiodobenzaldehyde (for hydrazones 1 and 2, respectively; 1.1 mmol; 411.3 mg) in boiling methanol for 2 h. The hydrazide-hydrazones spontaneously precipitated were crystallized from MeOH if necessary.29 |
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