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CAS No. : | 3619-22-5 | MDL No. : | MFCD00007607 |
Formula : | C8H10N2O | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | MFFVZXOPRXMVET-UHFFFAOYSA-N |
M.W : | 150.18 | Pubchem ID : | 77174 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
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 |
---|---|---|
89.4% | With acetic acid; In ethanol; at 70℃; for 5h; | General procedure: The Compound I (0.79 mmol)was dissolved in 10 mL of absolute ethanol. Then the mixture of R2-CHO (0.66 mmol), 10 mL acetic acid and 3 mL absolute ethanol was added dropwise at 70 °C. The mixture was refluxed for 5 h. The solvent was evaporated. The crude product was purified by flash chromatography (neutral Al2O3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; In methanol;Reflux; | General procedure: Isatin based Schiff bases (1-20) were synthesized in three steps,first an esterification carried out by reacting different carboxylicacid with methanol in sulphuric acid (2-3 ml) under reflux conditionfor 12-16 h. The completion of reaction was monitored byTLC. After completion of reaction, reaction mixture was extractedwith hexane to obtained pure esters. Then esters were refluxedwith hydrazine hydrate in methanol with few drops of glacial aceticacid for 3 h. After completion of reaction, reaction mixture waswashed with chloroform to obtained different hydrazides. Thesehydrazides (1mmole) each were than treated with different Isatin(1mmole) in methanol having catalytic amount of glacial acetic acidfor 2-4 h. Reaction completion was monitored through periodicTLC. After completion of reaction, reaction mixture was washedwith n-hexane to obtain our desired products (1-20). The structureof all compounds was established through EI-MS and 1H NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.53 g | With 3-Methylpyridine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃; for 36h; | 2-Chloro-1H-indole-6-carboxylic acid (1.95 g, 10 mmol) and p-methylbenzoylhydrazone(1.5 g, 10 mmol) was suspended in 40 mL of tetrahydrofuran,Then add EDC (3.2g),HOBt (2.1g) and 3-methyl pyridine (3.5mL),After stirring for 24 hours at room temperature,filter,The cake was washed with tetrahydrofuran to give an off-white solid.After drying, 3.05 g of dihydrazide was obtained.Used in the next step without purification.Referring to the method shown in Example 1, wherein "2-chloro-1H-indole-6-carboxylic acid" is replaced with <strong>[704-91-6]1H-<strong>[704-91-6]indazole-6-carboxylic acid</strong></strong>.In this embodiment,1H- indazol-6-carboxylic acid (1.62g, 10mmol),p-Methylbenzoylhydrazone (1.5g, 10mmol),Stir the reaction at room temperature for 36 hours.After drying, 2.53 g of dihydrazide was obtained.In step b,Burgess reagent (3.1g),Raise the temperature and reflux for 3 hours.Recrystallization from anhydrous ethanol gave compound 1-4 (2.13 g) as a white solid product.Yield 90percent. |
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 |
---|---|---|
72% | With potassium carbonate; In butan-1-ol; at 150℃; for 0.416667h;Microwave irradiation; | A mixture of <strong>[13338-63-1]2-(3,4,5-trimethoxyphenyl)acetonitrile</strong> (40, 414?mg, 2?mmol), 4-methylbenzohydrazide (300?mg, 2?mmol) and K2CO3 (415?mg, 3?mmol) in n-BuOH (15?mL) was stirred under microwave irradiation (150?C, 25?min). Then, 25?mL water was added, and the mixture was extracted with EtOAc. The combined organic layers were then washed with brine, dried, filtered, and concentrated. The resultant residue was purified by flash column chromatography (silica gel, PE/EA, 6/1 to 2/1) to afford the desired product 41 (yield: 72%) as a white soild. 1H NMR (600?MHz, CDCl3) δ 7.83 (2H, d, J?=?8.1?Hz), 7.13 (2H, d, J?=?8.0?Hz), 6.45 (2H, s), 4.01 (2H, s), 3.73 (3H, s), 3.67 (6H, s), 2.32 (3H, s); 13C NMR (150?MHz, CDCl3) δ 167.72, 159.20, 152.97, 139.68, 132.26, 129.29, 128.66, 127.28, 126.14, 105.53, 60.59, 57.93, 33.77, 21.21. MS (ESI) m/z 340.1 [M+H]+, 362.1 [M+Na]+, 338.1 [M?-?H]-. |