Dolbier HW Solutions 545 - p-nitroaniline The third...

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The reaction shown in the equation has been reported in the chemical literature and gave the benzylic bromide in 60% yield. Treatment of this bromide with dimethylamine gives the desired product. (The isolated yield was 83% by this method.) 22.39 ( a ) This problem illustrates the application of the Sandmeyer reaction to the preparation of aryl cyanides. Diazotization of p -nitroaniline followed by treatment with copper(I) cyanide con- verts it to p -nitrobenzonitrile. ( b ) An acceptable pathway becomes apparent when it is realized that the amino group in the prod- uct is derived from the nitro group of the starting material. Two chlorines are introduced by electrophilic aromatic substitution, the third by a Sandmeyer reaction. Two of the required chlorine atoms can be introduced by chlorination of the starting material,
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Unformatted text preview: p-nitroaniline. The third chlorine can be introduced via the Sandmeyer reaction. Reduction of the nitro group completes the synthesis of 3,4,5-trichloroaniline. The reduction step has been carried out by hydrogenation with a nickel catalyst in 70% yield. reduce NH 2 Cl Cl NO 2 2,6-Dichloro-4-nitroaniline Cl Cl Cl NO 2 1,2,3-Trichloro-5-nitrobenzene Cl Cl Cl NH 2 3,4,5-Trichloroaniline 1. NaNO 2 , HCl, H 2 O 2. CuCl Cl 2 NH 2 NO 2 p-Nitroaniline NH 2 Cl Cl NO 2 2,6-Dichloro-4-nitroaniline Cl Cl Cl NH 2 Cl Cl Cl NO 2 NH 2 Cl Cl NO 2 NH 2 NO 2 NH 2 NO 2 p-Nitroaniline CN NO 2 p-Nitrobenzonitrile 1. NaNO 2 , HCl, H 2 O 2. CuCN 1 CH 2 Br NC p-Cyanobenzyl bromide (CH 3 ) 2 NH Dimethylamine CH 2 N(CH 3 ) 2 NC p-Cyano-N , N-dimethylbenzylamine AMINES 639...
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