Electric Literature of 16452-01-0, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 16452-01-0, name is 3-Methoxy-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.
Step 1 : 6-Methyl-7-methoxy-quinolineglycerol(2.5 eq) FeSO4«7H2O( 0.03 eq)[0182] Using a minimal amount of dioxane, 3-methoxy-4-methylaniline (5.00 g, 36.5 mmol) was slowly added to a mixture of sodium m-nitrobenzenesulfonate (6.62 g, 29.4 mmol), MsOH (20 mL), and FeSO4*7H2O (0.39 g, 1.4 mmol) in a 10OmL round bottom flask heated to an internal temperature of 145-155 0C. Glycerol( 10.75 g, 116.8 mmol) was then added dropwise via addition funnel while keeping the internal temperature at 145-155C. After addition, the reaction was stirred in a 150 0C oil bath until LCMS indicated completion (4-6 h). After being cooled to rt, ice (2Og) was added, then the solution was neutralized with IO N NaOH (calculated to same eq of MsOH) at a speed to keep the internal temperature below 40 0C. A thick suspension appeared after addition, and this was extracted with EtOAc (50 mL x 3). The organic layer was filtered through a Celite pad to remove insoluble black particles and then purified by flash column chromatography on silica gel to give the desired product (5.0 g, 79%). MS (ES) mlz 174.1 (M+ H+).
The chemical industry reduces the impact on the environment during synthesis 3-Methoxy-4-methylaniline. I believe this compound will play a more active role in future production and life.
Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; FAN, Pinchen; GLEASON, Mark, M.; JAEN, Juan, C.; LI, Lianfa; MCMAHON, Jeffrey, P.; POWERS, Jay; ZENG, Yibin; ZHANG, Penglie; WO2010/54006; (2010); A1;,
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