Synthetic Route of 7149-75-9, 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. 7149-75-9, name is 4-Chloro-3-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.
To a refluxing slurry of disodium carbonate (0.9 g. 0.01 mol) in 10 mL MeOH wasadded simultaneously a solution of 1,5-dichloropentan-3-one (0.93 mL, 0.01 mol) in 5 mL MeOH and a solution of 4-chloro-3-methylaniline (1 g, 0.01 mol) in 5 mL MeOH dropwise over 10 mins. The reaction was allowed to reflux for a further 2.5 h, then allowed to cool and concentrated, poured into water (10 mL), and extracted with DCM (2 x lOmL). The combined organics were dried over MgSO4 and concentrated to yield 1.38 g free flowing orange/brown oil. The crude product was purified using column chromatography (Biotage, 50 g SNAP KP-SIL, 10 -80percent EtOAc in heptane, 10 CV) to yield the title compound as a light yellow free-flowing liquid (890 mg, 86percent purity, 48percent).1H NMR (500 MHz, Chloroform-d) delta 7.22 (d, J = 8.7 Hz, 1 H), 6.83 (d, J = 2.9 Hz, 1H), 6.74 (dd, J = 8.7, 3.0 Hz, lH), 3.56 (t, J = 6.1 Hz, 4H), 2.55 (t, J = 6.1 Hz, 4H), 2.35 (s, 3H). LCMS Method D: rt 1.33 min, 91 percent; m/z 223.95 (MH+)
The chemical industry reduces the impact on the environment during synthesis 4-Chloro-3-methylaniline. I believe this compound will play a more active role in future production and life.
Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; EVOTEC INTERNATIONAL GMBH; GAMPE, Christian, M.; KAHNE, Daniel, Evan; KAHNE, Suzanne, Walker; QIAO, Yuan; EAST, Stephen; PARKES, Alastair, L.; SOUTHEY, Michelle; HUNTER, James; WHITTAKER, Mark; ARTHUIS, Martin; (359 pag.)WO2016/191658; (2016); A1;,
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