3-Methoxy-2-methyl-1H-pyridin-4-one
3-Methoxy-2-methyl-1H-pyridin-4-one
CAS: 76015-11-7
Molecular Formula: C7H9NO2
3-Methoxy-2-methyl-1H-pyridin-4-one - Names and Identifiers
| Name | 3-Methoxy-2-methyl-1H-pyridin-4-one |
| Synonyms | Pantoprazole Impurity 41 3-methoxy-2-methyl-4-pyridone 4-Pyridinol, 3-methoxy-2-methyl- 4-pyridinol, 3-methoxy-2-methyl- 2-Methyl-3-methoxypyridine-4-one 3-Methoxy-2-Methyl-4-(1h)-Pyridone 2-methyl-3-methoxy-4(1H)-pyridinone 3-Methoxy-2-methyl-1H-pyridin-4-one 3-Methoxy-2-methyl-4(1H)-pyridinone 3-methoxy-2-methylpyridin-4(1H)-one 4(1H)-pyridinone, 3-methoxy-2-methyl- 3-METHOXY-2-METHYL-1H-PYRIDIN-4-ONE 97 |
| CAS | 76015-11-7 |
| EINECS | 616-282-9 |
| InChI | InChI=1/C7H9NO2/c1-5-7(10-2)6(9)3-4-8-5/h3-4H,1-2H3,(H,8,9) |
| InChIKey | GNWSQENQZGWCSW-UHFFFAOYSA-N |
3-Methoxy-2-methyl-1H-pyridin-4-one - Physico-chemical Properties
| Molecular Formula | C7H9NO2 |
| Molar Mass | 139.15 |
| Density | 1.12±0.1 g/cm3(Predicted) |
| Melting Point | 156-160 °C (lit.) |
| Boling Point | 252.7±40.0 °C(Predicted) |
| Flash Point | 106.6°C |
| Vapor Presure | 0.0191mmHg at 25°C |
| pKa | 11.07±0.69(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.516 |
3-Methoxy-2-methyl-1H-pyridin-4-one - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
3-Methoxy-2-methyl-1H-pyridin-4-one - Reference Information
| use | 3-methoxy-2-methyl-1H-pyridine-4-one can be used as an intermediate in pharmaceutical synthesis. It can be prepared by reacting maltol with iodomethane to prepare 2-methyl-3-methoxypyranone, and further reacting with ammonia water, it can be used to prepare the compound 2-methyl -3-hydroxy -1-((coumarin -3-yl) methyl) pyridin-4 (1H)-one, which has iron chelating and monoamine oxidase B inhibitory activities. |
| preparation | add maltol (7.56g,60mmol), acetone 100mL, methyl iodide (9.37g,66mmol) to a 250mL single-mouth bottle, heat and reflux for 6 hours, cool to room temperature after the reaction, spin dry solvent, add 100mL of water to dissolve, extraction with dichloromethane (50mL) 4 times, the organic layer is dried with anhydrous sodium sulfate, and the organic layer is concentrated to obtain 2-methyl-3-methoxypyrone. 98% yield. Pyranone (8.65g,40mmol) obtained by the above reaction was added into a 250mL single-mouth bottle, 60mL of 25% ammonia water and 50mL of ethanol were, heated and refluxed at 75 ℃ for 12h, cooled to room temperature after the reaction, dried the solvent to obtain brown oily liquid, recrystallized with acetone/ethyl acetate to obtain light yellow solid 3-methoxy -2-methyl -1H-pyridine -4-one. 75% yield. |
| Application | 3-methoxy-2-methyl-1H-pyridine-4-one can be used to prepare compounds 2-methyl-3-hydroxy-1-((coumarine-3-yl) methyl) pyridine-4 (1H)-one: 3-bromomethyl coumarin (717.2mg,3mmoL),3-methoxy -2-methyl -1H-pyridine -4-one (430.5mg,2mmol), potassium carbonate (414.6mg,3mmol), acetonitrile 12mL and water 1.5mL were added into a 25mL single-mouth flask. The reflux reaction was heated until the TLC detection reaction was completed. The solvent was removed by vacuum distillation, and the intermediate was obtained by column chromatography, and the yield was 59%. The yellow solid (373.41mg,1mmoL) obtained in the previous step was placed in a 50mL single-mouth flask, 15mL of anhydrous dichloromethane was added to dissolve, nitrogen was replaced for 3 times, and stirred at -48 ℃; 10mL of anhydrous dichloromethane solution 1.5 mL1.0mol/L boron tribromide (BCl3) was added into a constant pressure drop funnel, slowly dropped, kept warm for 2 hours, and transferred to room temperature for 12 hours to continue the reaction; Add 5mL methanol dropwise to quench, the solvent was removed by distillation under reduced pressure to obtain a yellow solid, and methanol/ether recrystallized to obtain 2-methyl-3-hydroxy-1-((coumarin -3-yl) methyl) pyridin-4 (1H)-one. 86% yield. |
Last Update：2024-04-09 21:01:54
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