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(Ar-NH2 to Ar-CN)


Example 1

To a suspension of CuCN (13.6 g, 152 mmol) in ACN (500 mL) was added isoamyl nitrite (25.4 mL, 190 mmol). A solution of the SM (20.0 g, 127 mmol) in ACN (100 mL) was added, and the reaction mixture was stirred at 65 C for 4 h. After completion, the mixture was diluted with H2O (500 mL) and extracted with EtOAc (2 x 500 mL). The org layer was dried (Na2SO4) and concentrated. The resulting crude material was purified by silica gel column chromatography (5% EtOAc/hexane) to provide the product as a brown solid. [5.0 g, 23.4%] [WO2014201173, page 239]