Extracurricular laboratory: Synthetic route of 46004-37-9

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To a suspension of methyl 4-amino-2- chlorobenzoate (20.0 g, 107.75 mmol) and CaCO3 (21.58 g, 215.5 mmol) in MeOH (216 mL) was added a solution of iodine monochloride (20.0 g, 123.2 mmol) in CH2CI2 (102 mL). The resulting reaction mixture was stirred at room temperature for 5 h, and quenched by adding cooled water (700 mL) and ethyl acetate (700 mL). It was filtered through celite, the filtrate was treated with 300 mL of 10% sodium thiosulfate, partitioned, and the aqueous layer was extracted with ethyl acetate (400 mL). The combined organic layers were washed with 10% sodium thiosulfate (2x), and brine. The organic layer was dried over Mg504, and concentrated to dryness under vacuum. The residue was adsorbed in silica gel, loaded into flash column which was eluted with 5, 7.5, and 10% ethyl acetate/toluene to afford 17.0 g of title compound as a yellow solid. 1H NMR (400 MHz, CDCI3): 6 8.26 (s, 1H),6.75 (s, 1H), 4.52 (bs, 1H), 3.87 (s, 3H). LCMS (M+1) 312.0, 314.0.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 4-amino-2-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING / MCGILL UNIVERSITY; TREMBLAY, Michel L.; PENAFUERTE, Claudia; FELDHAMMER, Matthew; ZOGOPOULOS, George; BLACK, Cameron; CRANE, Sheldon; TRUONG, Vouy-Linh; KENNEDY, Brian; WO2015/127548; (2015); A1;,
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