Electric Literature of 16452-01-0,Some common heterocyclic compound, 16452-01-0, name is 3-Methoxy-4-methylaniline, molecular formula is C8H11NO, 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.
Reference Intermediate R2 4-methyl-3-(methyloxy)phenol [1376] 4-methyl-3-(methyloxy)aniline (Reference Intermediate R1, 1.86 g) in water (100 mL)/ H2SO4 (30 mL, 563 mmol) at 0 C. a solution of sodium nitrite (1.029 g, 14.91 mmol) in water (10 mL) was slowly added and the reaction mixture was stirred for 30 minutes at 0 C. The reaction mixture was slowly added to a solution of H2SO4 98% (20 mL) in Water (80 mL) pre-heated at 90 C. and stirred at this temperature for 1 h. After cooling the mixture was extracted with Et2O (2×200 mL), the organic layer was dried on sodium sulphate, filtered and evaporated to afford the title compound (1.86 g) as a red/brown oil. [1378] 1H-NMR (400 MHz, DMSO-d6) delta ppm: 9.14 (1H, br.s), 6.87 (1H, d), 6.35 (1H, d), 6.24 (1H, dd), 3.71 (3H, s), 2.01 (3H, s); UPLC_B: 0.63 min, 137 [M-H]-.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methoxy-4-methylaniline, its application will become more common.
Reference:
Patent; AUTIFONY THERAPEUTICS LIMITED; Alvaro, Giuseppe; Dambruoso, Paolo; Tommasi, Simona; Decor, Anne; Large, Charles; US2013/267510; (2013); A1;,
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