Synthetic Route of 7149-75-9,Some common heterocyclic compound, 7149-75-9, name is 4-Chloro-3-methylaniline, molecular formula is C7H8ClN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
4-chloro-3-methylaniline (306 mg, 2.16 mmol) and tert-butyl 3- (bromomethyl)azetidine- l-carboxylate (450 mg, 1 .8 mmol) were stirred in acetonitrile (5 mL) under nitrogen, and KI (60 mg, 0.36 mmol) and K2CO3 (298 mg, 2.16 mmol) were added. The reaction was stirred at 85 °C for 48 h. The reaction was concentrated and partitioned between ethyl acetate and saturated sodium carbonate. The combined organics were dried over Na2S04, and concentrated. The crude product was purified by reverse phase column chromatography to yield the title compound as a white solid (31 1 mg, 54percent).1H NMR (500 MHz, Chloroform-d) delta 7.13 (d, J = 8.6 Hz, 1 H), 6.49 (d, J = 2.8 Hz, IH), 6.40 (dd, J = 8.6, 2.8 Hz, 1H), 4.07 (t, J = 8.4 Hz, 2H), 3.68 (dd, J = 8.7, 5.1 Hz, 2H), 3.33 (d, J = 7.3 Hz, 2H), 2,83 – 2.75 (m, IH), 2.32 (s, 3H), 1.46 (s, 9H). LCMS Method D: rt 1.52 min, 97percent; m/z 254.95 (MH+- Bu)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-3-methylaniline, its application will become more common.
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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