3-AMINO-4-METHYLBENZOIC ACID ETHYL ESTER synthesis

Yield:917391-29-8 54.1%

Reaction Conditions:

in ethyl acetate at 5 - 50; for 1.25 h;

Steps:

12

Example 12 4-Methyl-1 -(3-nitro-5-trif luoromethyl-phenyl)-1 H-imidazole methanesulfonic acid salt (XXIX)Crude 4-methyl-1-(3-nitro-5-trifluoromethyl-phenyl)-1 H-imidazole (IX) (1.85 g, 6 mmol, 88 area% purity in HPLC) is dissolved in ethyl acetate (6 ml_) at about 50 ⁰C. To the stirred resulting black solution is slowly added methanesulfonic acid (0.397 ml_, 6 mmol) at about 50⁰C. At the end of the addition a bright solid starts to precipitate. The mixture is allowed to slowly cool down to room temperature and is further stirred at about 5 ⁰C for 75 minutes. The solid formed is filtered, washed with ethyl acetate (4 ml_) and dried at room temperature and reduced pressure. A suspension of the obtained material in 2-propanol (5 mL) is stirred at 50 ⁰C for 90 minutes, is allowed to cool down to room temperature, stirred for 1 hour and at 0-5⁰C for another hour. The solid formed is filtered, washed with cold 2-propanol (5 mL) and dried at room temperature and reduced pressure to afford 4-methyl-1-(3-nitro-5- trifluoromethyl-phenyl)-1H-imidazole methanesulfonic acid salt as a beige solid. -Yield: 54.1% (HPLC purity: 99.5 area%), Melting point: 208-213°C

References:

WO2006/135640,2006,A2 Location in patent:Page/Page column 24