Methyl 4-chloro-3-nitrobenzoate

Methyl 4-chloro-3-nitrenzoate (1). Dissolve 4-chloro-3-nitro-benzoic acid (5.0 g, 24.8 mmol) in 200 ml of methanol and add 4.15 ml (29.8 mmol) of triethylamine. Cool in an ice-salt bath and add drop by drop 3.19 ml (44.7 mmol) of acetyl chloride. Agitate at reflux for 6 hours. Evaporate the solvent under reduced pressure. Take up the residue with 100 ml of water and extract 2 times with ethyl acetate (100 ml). Dry the organic phase on MgSOSynthesis of the 6-methoxycarbonyl-2-oxindole in accordance with the process shown in synthesis scheme C.Synthesis of benzoic acid, 4-chloro-3-nitro-, methylester20kg of 4-chloro-3-nitro-benzoic acid ( 99, 22mol) is suspended in 76L methanol. 5, 9kg thionylchloride (49, 62mol) is added within 15 minutes and refluxed for about 3 hours. After cooling to about 5°C, the product is isolated by centrifugation and drying at 45°C. Yield: 19, 0kg (88, 8percent of theoretical amount) : Synthesis of the 6-methoxycarbonyl-2-oxindole in accordance with the process shown in synthesis scheme C.; Synthesis of benzoic acid, 4-chloro-3-nitro-, methylester; 20kg of 4-chloro-3-nitro-benzoic acid ( 99, 22mol) is suspended in 76L methanol. 5, 9kg thionylchloride (49, 62mol) is added within 15 minutes and refluxed for about 3 hours. After cooling to about 5°C, the product is isolated by centrifugation and drying at 45°C. Yield: 19, 0kg (88, 8percent of theoretical amount) Purity (HPLC): 99, 8percentAfter 200g (1mol) 4-chloro-3-nitrobenzoic acid was suspended in methanol, Within 15 min, add 59g (490mmol) thionyl chloride. Heat at reflux. After reacting at 70 °C for 3 hours, cool to 5 °C, products pass through the centrifugal separation, the 45 °C drying, to obtain the solid 189.2g, the target compound, the yield is 88.5percent.4-Chloro-3-nitro benzoic acid (40.0g, 0.02mol) was suspended in methanol (200mL) and cooled down to 0°C. Concentrated sulfuric acid (22mL) was slowly added with stirring, and then the mixture was heated at reflux for 17h. Upon cooling to room temperature, a precipitate formed, which was collected by filtration and washed with cold methanol (2×30mL) and hexane (2×30mL) to afford the methyl ester as a white solid (35.5g, 83percent).a)

Molecular Weight:215.59
XLogP3:2.1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:214.9985354
Monoisotopic Mass:214.9985354
Topological Polar Surface Area:72.1
Heavy Atom Count:14
Complexity:240
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes