5-(Methoxymethyl)-2,3-pyridinedicarboxylic acid

The preparation methods are as follows. (1) In a three-necked flask of cyclization hydrolysis method, put in anhydrous ethanol, 2-methoxymethacrolein, dimethyl 3-chloro-2-oxosuccinate and sulfonamide successively, and stir at reflux for 15 h, then cool. After reaching room temperature, the solvent was removed under reduced pressure and extracted with ethyl acetate, and the finished product was separated by column chromatography. It is further hydrolyzed in acidic medium to obtain 5-methoxymethyl-2, 3-pyridinedicarboxylic acid. If 2-aminomaleic acid diethyl ester is used instead of 3-chloro-2-oxosuccinic acid dimethyl ester, 5-methoxymethyl-2, 3-pyridinedicarboxylic acid ethyl ester can also be obtained. (2) The epoxidation method dissolve an appropriate amount of methanol in concentrated sulfuric acid, heat it to 65°C, add o-aminophenol and o-nitrophenol, start stirring and heat up to 70°C, add methoxy methacrolein dropwise, then Incubate at 90°C for 1 hour, add 50% NaOH solution to adjust the pH to neutral, extract with chloroform, dry over anhydrous magnesium sulfate, filter, and desolvate the filtrate to obtain 3-methoxymethyl-8-hydroxyquinoline. Heat the above product in 50% NaOH to 85°C, slowly add 30% hydrogen peroxide solution dropwise, and control the temperature within 90°C. After the reaction is over, cool to room temperature to adjust the pH to acidity. After extraction and drying with chloroform, reduce Pressure desolventizes the crystallization to obtain the finished product. It is also possible to use nitric acid and manganese dioxide as the oxidant to oxidize 3-methoxymethyl-8-hydroxyquinoline, that is, to dissolve concentrated nitric acid and manganese dioxide in nitrobenzene, after heating to 95℃, slowly add dropwise to 3-Methoxymethyl-8-hydroxyquinoline in nitrobenzene, after dripping, react at 100℃ for 10h, cool to room temperature, filter to obtain N-nitropyridine compound, dissolve it in dichloromethane and In methyl isobutyl ketone, heat to reflux for 1 hour, cool, filter, rinse, and dry to obtain the finished product.

5-Methoxymethyl-2,3-pyridinedicarboxylic acid is an intermediate of the herbicide methoxam.

Molecular Weight:211.17
XLogP3:-0.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:211.04807239
Monoisotopic Mass:211.04807239
Topological Polar Surface Area:96.7
Heavy Atom Count:15
Complexity:255
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes