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Beckmann rearrangement of oximes leads to amides which may be reduced to amines: ΝΟΗ CCH3 H,SQ Acetophenone oxime |<^NNHCOCH3 LiAlH4 _ Acetanilide [7V-Ethylaniline NOH °H Polyphosphoric acid Heat Cyclohexanone oxime r^^NHCH Nv { ] LiAlH4 Nv ^ Caprolactam Azacycloheptane Of course, amides need not necessarily be obtained from oximes. They are usually obtained from the appropriate acids or esters. CONH, I " CH 3 u NCOCH3 CH3COC1 ^ N JV-Methylacetanilide Heat I 90% CH,CONH, O^^N^^O H Succinamide Succinimide ΓΠ ,/V,JV-Methylethylaniline X——1 1 u NC2H, UA1H„ L1AIH4 LiAlH Ό I 1 ^N" H Pyrrolidine 44 CONCERNING AMINES REDUCTION OF CYANIDES Cyanides are suitable starting materials for the preparation of primary amines by complete saturation of the C = N triple bond.

In the industrial preparation of aniline, nitrobenzene is reduced with iron filings and 30% hydrochloric acid. After completion of the reaction the mixture must be neutralized with sodium carbonate and the aniline is removed by steam distillation. Aniline is somewhat soluble in water, sufficiently so that this factor must be considered in the industrial process. The soluble PROPERTIES, PREPARATION AND REACTIONS 21 aniline is salted out by the addition of common salt. ) Two layers are then obtained, one of 20% sodium chloride solution and the other of aniline.

It works fairly well with many secondary halides, RR'CHX but the reaction is useless where tertiary halides are concerned. The reason for this is that ammonia and amines are bases and may therefore bring about an elimination reaction as well as the desired substitution. The latter reaction predominates in primary halides. ) This is a much more difficult reaction to carry out than in the respective 0- or/7-nitro substituted chlorobenzenes. The following reactions proceed with much greater ease because electronwithdrawal from the ring by the nitro group aids nucleophilic substitution at the halogen-substituted carbon atom.

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