1-Methyl 3-nitro-1,2-benzenedicarboxylate

light yellow crystalline powder

3-Nitrophthalic acid (500 g, 2.37 moles) was added to 2500 ml of methanoland 260 ml of thionyl chloride below ambient temperature. The mixture washeated at reflux for about 24 hours and then was concentrated under reducedpressure, followed by expelling the excess thionyl chloride under nitrogen. 1500ml of toluene was mixed with the residue, and then filtered. The obtained solidwas dried at 60-70°C to get 522.0 grams (98percent) of methyl 2-carboxyl-3-nitrobenzoate, which was substantially free from 3-nitrodimethylphthalate; 500 g of 3-Nitrophthalic acid, and methanol (2.5 I) were charged in a roundbottom flask followed by cooling to about 5-10°C. 259.5 ml of thionyl chloride wasadded under stirring for about 60-90 minutes followed by heating to about 60-65°C and was maintained for about 20-25 hours. Solvent was distilled completelyat about 60-65°C; 1500 ml of toluene was added and stirred for about 5-6 hoursunder nitrogen atmosphere. Separated solid was filtered and washed with 500mlof toluene, followed by drying the solid at about 55-65°C for about 5-10 hours toafford 525 grams of 3-nitrophthalic acid-1-methylester compound of Formula (II).3-Nitrophthalic acid [NPA] (660 kg), trimethyl orthoformate (400 kg), concentrated sulfuric acid (115 kg) and methanol (1180 kg) were mixed, and the mixture was stirred with heating (59 to 65 °C) for about 15 to 20 hours under reflux.. (1) Put 30 g of 3-nitrophthalic acid into a 500 ml reaction flask and add 300 ml of methanol (1:10, optionally 1:5 to 1:20, preferably 1:10 to 1:15). Sulfuric acid 30g (1:0.5-1:2, preferably 1:1) was warmed at reflux.(2) TLC monitoring, when the formation of the double esterification product exceeds the reduction of the raw material, the refluxing reaction is ended; below 50° C., the methanol is concentrated under reduced pressure to almost no fraction.(3) Add 200ml of water, control the temperature below 25°C, add potassium carbonate to neutralize the pH to 7-8, and add 100ml of ethyl acetate to extract.The extract is concentrated and crystallized to obtain dimethyl 3-nitrophthalate, the aqueous layer is acidified to pH 4-5, stirred at room temperature for 2 hours, and the product is filtered to obtain methyl 3-nitro-2-carboxybenzoate (AM1). , Content more than 98percent, yield more than 90percent, Drying standby.

Molecular Weight:225.15
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:225.02733694
Monoisotopic Mass:225.02733694
Topological Polar Surface Area:109
Heavy Atom Count:16
Complexity:310
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes