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CAS No. : | 13025-99-5 | MDL No. : | N/A |
Formula : | C12H10N4O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RVAFAIOWXGOYMP-OQLLNIDSSA-N |
M.W : | 226.23 | Pubchem ID : | 5469567 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
96% | With hydrogenchloride In ethanol Microwave irradiation; | 4.2.1.2 Microwave irradiation (MWI) General procedure: 3-Pyridinecarboxaldehyde (1) and/or 4-pyridinecarboxaldehyde (2) (1mmol), 43 ethanol (5mL), isonicotinic acid hydrazide (44 3) (1mmol) and few drops of 45 hydrochloric acid were placed in closed 46 borosilicate glass vessel fitted with a silicone cap and exposed to irradiation for 2-3min using a microwave reactor. The reaction was processed as described in the conventional procedure outlined earlier to give the same targets 47 4 and/or 5. |
92% | With hydrogenchloride In ethanol for 1h; Reflux; | 2 Synthesis of N'-(pyridinylmethylene)isonicotino hydrazide derivatives 2 and/or 3 General procedure: To a mixture of isonicotinic acid hydrazide (1) (1 mmol) in ethanol(25 ml) was added 4-pyridinecarboxaldehyde and/or 3-pyridinecarboxaldehyde (1.2 mmol) and few drops of hydrochloricacid, then the mixture was refluxed for 1 h. After cooling, the excessof solvent was removed under reduced pressure. The product formed was recrystallized from ethanol to furnish the desired compounds.3.1.2 (E)-N'-(Pyridin-4-ylmethylene)isonicotinohydrazide (2) It was obtained as yellow crystals in 92% yield; mp: 223-224 °C (Lit. mp: 224-225 °C) [ 41 ]. 1H NMR (400 MHz, DMSO-d6): δH = 7.57 (d, 0.25H, J = 4 Hz, Ar-H), 7.71 (d, 0.25H, J = 4 Hz, Ar-H), 7.82 (d, 1.75H, J = 8 Hz, Ar-H), 7.90 (dd, 1.75H, J = 4 Hz, 8 Hz, Ar-H), 8.14 (s, 0.2H, H-C=N), 8.55 (s, 0.8H, H-C=N), 8.66 (d, 0.25H, J = 4 Hz, Ar-H), 8.74 (d, 1.75H, J = 4 Hz, Ar-H), 8.79 (d, 0.25H, J = 4 Hz, Ar-H), 8.84 (dd, 1.75H, J = 4 Hz, 8 Hz, Ar-H), 12.47 (s, 0.2H, CONH), 12.58 (s, 0.8H, CONH). 13C NMR (100 MHz, DMSO-d6): δC = 121.32, 121.62, 121.76, 123.28, 140.14, 142.58, 146.21, 149.21, 149.48, 150.38 (Ar-C), 162.08, 162.10 (C=N, C=O). HRMS (ESI) m/z = 226.1414 [M+]. |
90% | With hydrogenchloride In ethanol at 20℃; for 0.5h; |
90% | In ethanol for 6h; Heating; | |
83% | In ethanol at 100℃; | General procedure: The dried hydrazide and the corresponding aldehyde (1eq) were dissolved in EtOH and refluxed at 100°C for 3-4h, then cooled to room temperature and the crystals precipitated, which are filtered and dried to obtain the final products (1-15). |
With water | ||
With acetic acid In ethanol | ||
In methanol at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | at 60℃; Sealed tube; | Synthesis of [Hg(L1)I2] (1), [Hg(L2)2I2] (2) and [Hg(μ-L3)I2]n (3) 2-pyridine piconyl hydrazone (L1) (0.181 g, 0.5 mmol) and mercury(II) iodide (0.254 g, 0.5 mmol) were transferred to the main arm of a branched tube, with subsequent addition of methanol to fill the arms. The tube was sealed and immersed in an oil bath temperature controlled at 60 °C while keeping the branched arm at ambient temperature. After 24 h, crystals of 1 forming on surface of the cooler arm were removed by filtration, further purified by washing with acetone and ether, and ultimately dried in air. Crystals of 2 and 3 were prepared by combining appropriate ligand with mercury(II) iodide, following the same procedure as for 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | for 0.416667h; Milling; Green chemistry; | |
for 0.416667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
for 0.416667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With potassium hydroxide In ethanol; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With potassium hydroxide In ethanol; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide In methanol; water at 110℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide In methanol; water at 110℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: potassium hexafluorophosphate / acetonitrile / 16 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: acetonitrile / 16 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: acetonitrile / 16 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: potassium hexafluorophosphate / acetonitrile / 16 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: acetonitrile / 16 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: acetonitrile / 16 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: potassium hexafluorophosphate / acetonitrile / 16 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: acetonitrile / 16 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / Reflux 2: acetonitrile / 16 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In acetonitrile Reflux; | 1 General procedures for the synthesis of dipyridinium ionic liquids tethered hydrazones 4-9 General procedure: A mixture of compound 2 and/or 3 (1mmol) in acetonitrile (30ml) and the appropriate phenacyl bromide (2.1mmol) was refluxed for 6-12h. The solvent was reduced by evaporation under reduce pressure, the precipitate formed was collected by filtration and/or extraction by chloroform to afford the desired dicationic liquids 4-9. 3.2.1 1-(2-(4-Methoxyphenyl)-2-oxoethyl)-4-((2-(1-(2-(4-methoxyphenyl-2-oxoethyl)pyridin-1-ium-4-carbonyl) hydrazono) methyl)pyridin-1-ium bromide (4) It was obtained as syrup in 88% yield. 1H NMR (400 MHz, DMSO-d6): δH = 3.92 (s, 6H 2 * OCH3), 6.58 (d, 4H, J = 8 Hz, 2 * NCH2), 7.22 (d, 4H, J = 8 Hz, Ar-H), 8.09 (d, 4H, J = 8 Hz, Ar-H), 8.29 (d, 0.5H, J = 4 Hz, Ar-H), 8.40 (d, 0.5H, J = 4 Hz, Ar-H), 8.52 (s, 0.25H, H-C=N), 8.57 (d, 1.5H, J = 8 Hz, Ar-H), 8.71 (d, 1.5H, J = 4 Hz, Ar-H), 8.78 (s, 0.75H, H-C=N), 8.97 (d, 0.5H, J = 4 Hz, Ar-H), 9.07 (d, 1.5H, J = 8 Hz, Ar-H), 9.19 (d, 0.5H, J = 4 Hz, Ar-H), 9.28 (d, 1.5H, J = 4 Hz, Ar-H), 13.37 (s, 0.25H, CONH), 13.42 (s, 0.75H, CONH). 13C NMR (100 MHz, DMSO-d6): δC = 56.32 (2 * OCH3), 66.12; 66.76 (2 * NCH2), 141.92; 125.13; 126.75; 127.56; 131.25; 131.30; 145.04; 147.23; 147.76; 147.89; 149.83 (Ar-C), 160.54; 164.79 (C=N, C=O), 189.08; 189.46 (2 * CH2C=O). HRMS (ESI) m/z = 684.3530 [M+]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In acetonitrile Reflux; | 2 General procedures for the synthesis of dipyridinium ionic liquids tethered hydrazones 4-9 General procedure: A mixture of compound 2 and/or 3 (1mmol) in acetonitrile (30ml) and the appropriate phenacyl bromide (2.1mmol) was refluxed for 6-12h. The solvent was reduced by evaporation under reduce pressure, the precipitate formed was collected by filtration and/or extraction by chloroform to afford the desired dicationic liquids 4-9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In acetonitrile Reflux; | 3 General procedures for the synthesis of dipyridinium ionic liquids tethered hydrazones 4-9 General procedure: A mixture of compound 2 and/or 3 (1mmol) in acetonitrile (30ml) and the appropriate phenacyl bromide (2.1mmol) was refluxed for 6-12h. The solvent was reduced by evaporation under reduce pressure, the precipitate formed was collected by filtration and/or extraction by chloroform to afford the desired dicationic liquids 4-9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With potassium hydroxide In methanol at 110℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
for 0.416667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
for 0.416667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In methanol at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In methanol at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide In methanol; water at 100℃; for 6h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide In methanol at 100℃; for 6h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | In acetonitrile for 0.05h; Microwave irradiation; | 4.1 4.2.3.2 Microwave irradiation (MWI) General procedure: Dipyridine Schiff base 4 and/or 5 (1mmol), acetonitrile (5mL), and the appropriate bromoalkoxybenzene derivatives (2mmol) were placed in closed borosilicate glass vessel fitted with a silicone cap and exposed to irradiation for 3-4min using a microwave reactor. The reaction was processed as described in the conventional procedure outlined earlier to give the same dicationic pyridinium bromides 6-11. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In acetonitrile for 0.05h; Microwave irradiation; | 4.2 4.2.3.2 Microwave irradiation (MWI) General procedure: Dipyridine Schiff base 4 and/or 5 (1mmol), acetonitrile (5mL), and the appropriate bromoalkoxybenzene derivatives (2mmol) were placed in closed borosilicate glass vessel fitted with a silicone cap and exposed to irradiation for 3-4min using a microwave reactor. The reaction was processed as described in the conventional procedure outlined earlier to give the same dicationic pyridinium bromides 6-11. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In acetonitrile for 0.0666667h; Microwave irradiation; | 4.3 4.2.3.2 Microwave irradiation (MWI) General procedure: Dipyridine Schiff base 4 and/or 5 (1mmol), acetonitrile (5mL), and the appropriate bromoalkoxybenzene derivatives (2mmol) were placed in closed borosilicate glass vessel fitted with a silicone cap and exposed to irradiation for 3-4min using a microwave reactor. The reaction was processed as described in the conventional procedure outlined earlier to give the same dicationic pyridinium bromides 6-11. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 0.07 h / Microwave irradiation 2: acetonitrile / 0.17 h / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 0.07 h / Microwave irradiation 2: acetonitrile / 0.17 h / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 0.07 h / Microwave irradiation 2: acetonitrile / 0.17 h / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 0.05 h / Microwave irradiation 2: potassium hexafluorophosphate / acetonitrile / 0.17 h / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 0.05 h / Microwave irradiation 2: acetonitrile / 0.17 h / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 0.05 h / Microwave irradiation 2: acetonitrile / 0.17 h / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 0.05 h / Microwave irradiation 2: acetonitrile / 0.17 h / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 0.05 h / Microwave irradiation 2: acetonitrile / 0.17 h / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 0.05 h / Microwave irradiation 2: potassium hexafluorophosphate / acetonitrile / 0.17 h / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 0.05 h / Microwave irradiation 2: acetonitrile / 0.17 h / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 0.05 h / Microwave irradiation 2: acetonitrile / 0.17 h / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 0.05 h / Microwave irradiation 2: acetonitrile / 0.17 h / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 0.05 h / Microwave irradiation 2: acetonitrile / 0.17 h / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 0.07 h / Microwave irradiation 2: potassium hexafluorophosphate / acetonitrile / 0.17 h / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: acetonitrile / 0.07 h / Microwave irradiation 2: acetonitrile / 0.17 h / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In ethanol at 90℃; for 72h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Stage #1: methanol; (E)-N′-(pyridin-4-ylmethylene) isonicotinohydrazide; terephthalic acid With sodium hydroxide for 0.25h; Stage #2: cobalt(II) perchlorate hexahydrate In water at 20℃; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium hydroxide In ethanol; water at 20℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sulfuric acid / 2 h / 85 - 95 °C 2: hydrazine hydrate / ethanol / 80 °C 3: ethanol / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol / 80 °C 2: ethanol / 100 °C |
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