These common heterocyclic compound, 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, its 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. category: nitriles-buliding-blocks
10% Palladium on carbon (5.06 g) was added under an atmosphere of nitrogen to a chilled (ice- water bath) solution of 2-(3 -methyl- IH-1, 2,4- triazol-l-yl)-5-nitrobertzonitrile (10.9 g, 47.6 mmol) dissolved in methanol (100 mL). The flask was repeated evacuated and flushed with hydrogen gas (double balloon). The resulting mixture was allowed to warm to rt and left to stir for 16 h under the hydrogen atmosphere. Purged with nitrogen gas. Filtered the crude reaction mixture through a short dialomaceous earth (Celite ) plug. Rinsed reaction vessel and plug with methanol. Concentrated filtrate in vacuo. Dried residue on high vacuum overnight to afford 5-amino-2-(3-methyl-lH-l,2,4-triazol-l-yI)benzonitrile (6.59 g, 70 % yield) as a brown solid. LC-MS (M+H)+ 200.0. 1H NMR (500 MHz, DMSO- J6) delta ppm 2.29 – 2.37 (m} 3 H) 5.99 (s, 2 H) 6.94 (dd, J=8.85, 2.44 Hz, 1 H) 7.00 (d, J-2.44 Hz, 1 H) 7.37 (d, J=8.54 Hz, 1 H) 8.69 – 8.81 (m, 1 H).
The synthetic route of 2-Chloro-5-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MARCIN, Lawrence, R.; THOMPSON, Lorin, A., III; BOY, Kenneth, M.; GUERNON, Jason, M.; HIGGINS, Mendi, A.; SHI, Jianliang; WU, Yong-Jin; ZHANG, Yunhui; MACOR, John, E.; WO2010/83141; (2010); A1;,
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