N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:8].[C:9](#[N:12])[CH:10]=[CH2:11].N(OC(C)C)=O>C(#N)C>[Cl:8][CH:10]([CH2:11][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]#[N:12]A mixture of 2.28 g (25 mmols) of distilled aniline, 30 mL of acetonitrile, 2.6 mL (31 mmols) of concentrated hydrochloric acid, 30 mL (456 mmols) of distilled acrylonitrile (AN), and 0.36 g (2.5 mmols) of cuprous oxide was stirred for five minutes under nitrogen. A mixture of 2.8 g (31 mmols) of isopropyl nitrite (IPN) and 30 mL of acetonitrile was added dropwise over a period of 20 minutes. The mixture warmed to 45° C. and nitrogen gas evolved. After stirring at ambient temperature for two hours, the dark mixture was worked up to provide an 84% yield of 2-chloro-3-phenylpropionitrile (CPPN).
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