Electric Literature of 59681-66-2,Some common heterocyclic compound, 59681-66-2, name is 4-Chloro-N1-methylbenzene-1,2-diamine, molecular formula is C7H9ClN2, 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.
[000316] To a solution of Compound 10B (2.5 g, 16 mmol) in methanol (50 mL) was added triethoxymethane (2.8 g, 19 mmol) and sulfamic acid (155 mg, 1.6 mmol). The mixture was stirred at rt for 5 h. After removal of solvents, the mixture was diluted with water (30 mL) and extracted with ethyl acetate (50 mL x 3). The organic layer was dried over Na2S04. Filtration and evaporation of solvents gave a crude product Compound IOC (2.3 g, crude) as a red solid, which was used to next step without purification. LC-MS (m/z): 167 [M+l]+; 1H-NMR (CDC13, 400 MHz) major characteristic peaks: delta (ppm) 3.84 (s, 3H), 7.30 (d, J= 8.4 Hz, 1H), 7.61 (d, J= 8.8 Hz, 1H), 7.70 (s, 1H), 8.25 (s, 1H).
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-N1-methylbenzene-1,2-diamine, its application will become more common.
Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; BRIDGES, Alexander, James; WO2015/42397; (2015); A1;,
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