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Dolbier HW Solutions 520 -...

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m -nitrocumene as only a minor component of the nitration product. However, the conversion of 4-isopropyl-2-nitroaniline to m -isopropylnitrobenzene, which was used to illustrate reductive deamination of arylamines in the text, establishes the last step in the synthesis. Our task simpli fi es itself to the preparation of 4-isopropyl-2-nitroaniline from cumene. The follow- ing procedure is a straightforward extension of the reactions and principles developed in this chapter. Reductive deamination of 4-isopropyl-2-nitroaniline by diazotization in the presence of ethanol or hypophosphorous acid yields m -nitrocumene and completes the synthesis. 22.21 Amines may be primary, secondary, or tertiary. The C 4 H 11 N primary amines, compounds of the type C 4 H 9 NH 2 , and their systematic names are
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Unformatted text preview: tert-Butylamine (2-methyl-2-propanamine) (CH 3 ) 3 CNH 2 sec-Butylamine (2-butanamine) CH 3 CHCH 2 CH 3 NH 2 Butylamine (1-butanamine) CH 3 CH 2 CH 2 CH 2 NH 2 Isobutylamine (2-methyl-1-propanamine) (CH 3 ) 2 CHCH 2 NH 2 HNO 3 H 2 SO 4 HO 2 , H 2 O, or 1. H 2 O, H 1 2. HO 2 CH(CH 3 ) 2 CH(CH 3 ) 2 NHCCH 3 NO 2 CH(CH 3 ) 2 NO 2 NH 2 O NHCCH 3 O p-Isopropylacetanilide 4-Isopropyl-2-nitroacetanilide 4-Isopropyl-2-nitroaniline CH(CH 3 ) 2 Cumene CH(CH 3 ) 2 NO 2 p-Nitrocumene CH(CH 3 ) 2 NH 2 p-Isopropylaniline CH(CH 3 ) 2 NHCCH 3 O p-Isopropylacetanilide HNO 3 H 2 SO 4 1. Fe, HCl 2. HO 2 CH 3 CCl O CH(CH 3 ) 2 Cumene CH(CH 3 ) 2 NH 2 NO 2 4-Isopropyl-2-nitroaniline CH(CH 3 ) 2 NO 2 m-Nitrocumene 614 AMINES...
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