Name | 5-Methoxymethyl-2,3-pyridinedicarboxylic acid |
Synonyms | Imazamox Impurity 15 5-(Methoxymethyl)pyridine-2,3-dicarboxylicaci 5-Methoxymethyl-2,3-pyridinedicarboxylic acid 5-METHYLMETHOXY-2,3-PYRIDINEDICARBOXYLIC ACID 5-(methoxymethyl)pyridine-2,3-dicarboxylic acid 5-(MethoxyMethyl)pyridine-2,3-dicarboxylic acid 5-(Methoxymethyl)-2,3-pyridinedicarboxylic acid |
CAS | 143382-03-0 |
InChI | InChI=1/C9H9NO5/c1-15-4-5-2-6(8(11)12)7(9(13)14)10-3-5/h2-3H,4H2,1H3,(H,11,12)(H,13,14) |
Molecular Formula | C9H9NO5 |
Molar Mass | 211.17 |
Density | 1.437 |
Melting Point | 140 - 145°C |
Boling Point | 428.61°C at 760 mmHg |
Flash Point | 213.016°C |
Solubility | DMSO (Slightly), Methanol (Slightly) |
Vapor Presure | 0mmHg at 25°C |
Appearance | Solid |
Color | Pale Yellow |
Storage Condition | 2-8°C |
Refractive Index | 1.589 |
Physical and Chemical Properties | This product is solid and insoluble in water. |
Uses | 5-methoxymethyl-2, 3-pyridinedicarboxylic acid is an intermediate of the herbicide methoxymidis. |
production method | the preparation method is as follows. (1) Anhydrous ethanol, 2-methoxymethacrolein, dimethyl 3-chloro-2-oxosuccinate and sulfonamide were successively put into the three-mouth bottle by cyclization hydrolysis method, heated, refluxed and stirred for 15 h, cooled to room temperature, decompressed and desolated, extracted with ethyl acetate, and separated by column chromatography to obtain the finished product. Further hydrolysis in an acidic medium to obtain 5-methoxymethyl-2, 3-pyridine dicarboxylic acid. If diethyl 2-aminomaleate is used instead of dimethyl 3-chloro-2-oxosuccinate, ethyl 5-methoxymethyl-2, 3-pyridine dicarboxylate can also be obtained. (2) Cyclic oxidation method Dissolve appropriate amount of methanol in concentrated sulfuric acid, heat to 65 ℃, add o-aminophenol and o-nitrophenol, start stirring and raise the temperature to 70 ℃, add methoxymethacrolein dropwise, then keep the temperature at 90 ℃ for 1h, add 50% NaOH solution to adjust the pH value to neutral, then extract with chloroform, dry with anhydrous magnesium sulfate, filter, and dedissolve the filtrate to obtain 3-methoxymethyl-8-hydroxyquinoline. Heat the above product in 50% NaOH to 85 ℃, slowly add 30% hydrogen peroxide solution dropwise, control the temperature within 90 ℃, after the reaction, cool to room temperature to adjust the pH value to acidic, extract and dry with chloroform, and dedissolve and crystallize to obtain the finished product. It is also possible to use nitric acid and manganese dioxide as oxidants to oxidize 3-methoxymethyl-8-hydroxyquinoline, that is, to dissolve concentrated nitric acid and manganese dioxide in nitrobenzene, and after the temperature is raised to 95°C, slowly add and dissolve in nitrobenzene in drops 3-methoxymethyl-8-hydroxyquinoline, after dropping, react at 100°C for 10h, cool to room temperature, and filter to obtain N-nitropyridine compound, dissolve it in dichloromethane and methyl isobutyl ketone, heat and reflux for 1h, cool, filter, rinse, and dry to obtain the finished product. |