Methyl 5-nitro-2-methylbenzoate

White crystalline powder

A solution of 2-methyl-5-nitrobenzoic acid (15 g, 82.8 mmole) in DMF (75 mL) was treated with methyl iodide (6.7 mL, 107.64 mmole) followed by powdered K2CO3 (17.2 g, 124.2 mmole) (extreme exotherm) and the suspension stirred at ambient temperature overnight. The reaction mixture was partitioned between EtOAc and water, the organics separated and washed with water and brine, dried (Na2SO4) and concentrated in vacuo to yield K1 (15.86 g, 98percent) in pure form as an off-white solid. The 1H NMR was consistent with that of the desired structure.4.2.1 23.2 g (88 mmol) of 2-iodo-4-nitrotoluene are dissolved in 400 ml of anhydrous methanol and then placed in a steel reactor. 25 ml (177 mmol) of triethylamine, 1.97 g (8.8 mmol) of palladium diacetate and 7.3 g of diphenyphosphinopropane are added and the reaction medium is subjected to a carbon monoxide pressure of 4 bar and heated at 110° C. for 18 hours. The medium is then brought to ambient pressure and temperature, dissolved in dichloromethane and filtered on celite. After evaporation, the residue is purified by chromatography on a silica column. An orange-coloured powder is obtained (m=6.3 g, Y=37percent).2-Methyl-5-nitrobenzoic Acid Methyl Ester (35). To a stirring MeOH (4 mL) in a round-bottom flask was added dropwise thionyl chloride (0.24 mL, 3.3 mmol) at 0° C. The mixture was added 2-methyl-5-nitrobenzoic acid 34 (300 mg, 1.7 mmol) at 0° C. and it was allowed to stir for 4 h at reflux temperature. The reaction was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give corresponding compound 35 (320 mg, 99percent) as a colorless oil, R2-Methyl-5-nitrobenzoate (5.0 g, 27.6 mmol) was dissolved in [MEOH] (0.4 L) followed by the addition of H2SO4 (7 mL). The mixture was heated at reflux for 36 h, then cooled [TO RT] and concentrated to ca 100 mL. The solution was diluted with [MTBE] neutralized with 6N [NAOH, ] washed with 1N [NAOH, ] brine, dried [(MGS04), ] filtered and concentrated in vacuo to afford 4.72 g (87percent) of methyl [2-METHYL-5-NITROBENZOATE] as a white solid.To a solution of compound 2 (64.0 g, 0.39 mol) in MeOH (1500 mL), H

Molecular Weight:195.17
XLogP3:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:195.05315777
Monoisotopic Mass:195.05315777
Topological Polar Surface Area:72.1
Heavy Atom Count:14
Complexity:236
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes