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CAS No. : | 80047-24-1 | MDL No. : | MFCD09800601 |
Formula : | C12H11N3O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SWKVSFPUHCMFJY-UHFFFAOYSA-N |
M.W : | 229.23 | Pubchem ID : | 12799331 |
Synonyms : |
|
Chemical Name : | 2-Methyl-6-oxo-1,6-dihydro-[3,4'-bipyridine]-5-carboxamide |
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: |
* 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 |
---|---|---|
72% | With sulfuric acid; at 120℃; for 0.25h;Inert atmosphere; | Concentrated sulfuric acid (350 L, 6.3 mmol, 14 equivalents) was added to 6-methyl-2-oxo-5-(pyridin-4-yl)-1,2-dihydropyridine-3-carbonitrile (95 mg, 0.450 mmol, 1 equivalent), and the solution was heated to 120 C for 15 minutes. The solution was then cooled to 0 C and diluted with water, whereupon concentrated ammonium hydroxide was added to bring the pH to 10. The resulting precipitate was filtered and dried to give the desired product as a white solid (74 mg, 72%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With bromine; sodium hydroxide; at 0 - 120℃; for 3.0h;Inert atmosphere; | 6-Methyl-2-oxo-5-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide (60 mg, 0.262 mmol, 1 equivalent) was dissolved in 1 M NaOH (1.5 mL) with heating and then cooled to 0 C. Bromine (16 L, 0.314 mmol, 1.2 equivalents) was then added dropwise and the reaction mixture heated to 120 C for 3 hours then cooled. The solution was then adjusted to pH = 7 with HCl (1 M) and cooled to 0 C for 2 hours. The precipitate was then filtered and washed with water to give the desired product as an off-white solid (12 mg, 23%). |
With sodium hydroxide; bromine; In hydrogenchloride; water; | D-1. 3-Amino-6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone, alternatively named 5-amino-2-methyl-[3,4'-bipyridin]-6(1H)-one-- To a solution containing 13 g. of sodium hydroxide in 250 cc. of water was added 12 g. of <strong>[80047-24-1]1,2-dihydro-6-methyl-2-oxo-5-(4-pyridinyl)nicotinamide</strong> and the resulting mixture was heated on a steam bath to effect dissolution. To the solution was added another 250 cc. of water and the resulting solution cooled to about 35 C. with stirring whereupon some crystals separated. The mixture was chilled in an ice bath and to it was added dropwise a total of 4.0 cc. of bromine, dissolution resulting after about 3 cc. of the bromine had been added. The mixture was stirred for an additional 10 minutes while cold and then was heated on a steam bath for 45 minutes. The reaction mixture was then concentrated to about 1/2 its volume, cooled in an ice bath and treated with 6 N hydrochloric acid until the pH was about 8. The resulting crystalline product was collected, rinsed twice with water and once with acetone, and dried to yield 7.3 g. of material. The 7.3 g. was treated with 20 cc. of water and the insoluble amorphous material was filtered off. The filtrate was concentrated to dryness and the resulting crystalline material was recrystallized from dimethylformamide-water to yield 3.8 g. of 3-amino-6-methyl-5-(4-pyridinyl)-2(1H)-pyridinone, m.p. >300 C. Acid-addition salts of 3-amino-6-methyl-5-(4-pyridinyl)2(1H)-pyridinone are conveniently prepared by adding to a mixture of 2 g. of 3-amino-6-methyl-5-(4-pyridinyl)-2(1H)-pyridine in about 40 ml. of aqueous methanol the appropriate acid, e.g., methanesulfonic acid, concentrated sulfuric acid, concentrated phosphoric acid, to a pH of about 2 to 3, chilling the mixture after partial evaporation and collecting the precipitated salt, e.g., dimethanesulfonate, sulfate, phosphate, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | 5-(4-Pyridyl)-3-carbamoyl-6-methyl-pyridine-2(1H)-one Yield 62%. M.p.>300 C. |
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