1- Amino-2,4-dinitronaphthalene

Dinitronaphthalene (Delta-dinitronaphtha-lenet 1,6-DNN). Crysts from acet ac, mp 166-67°, bp at 10mm 235°, 360° with decompn (Refs 2 31) CA Registry No 60746-5. It is prepd by the nitration of 2-nitronaphtha- ene with nitric ac/sulfuric ac in hot acet ac (Ref 21) by diazotization of 5-nitro-2-naphthyl-amine followed by treatment of the diazonium salt with Na cobaltinitrite, yield 40% (Ref 36) or by removal of the amino group from 1,6-dinitro-2-naphthylamine by diazotization followed by redn (Ref 17). The temp of expin is 492°(Refl7)... 

In some unusual cases, the amino group bonded to activated substrates may be replaced by primary amines, as in the case of the reaction of 2,4-dinitronaphthalene derivatives235, illustrated by Scheme 12. 

Nitropyridine yields a mixture of 2-, 4- and 6-amino-3-nitropyridines by this method142. An amino group is introduced into the 2-position of l,n-dinitronaphthalenes (.n = 3-8)143 and various 5- and 8-nitroquinolines, such as 8-methyl-5-nitroquinoline and 6-chloro-8-nitroquinoline, have been aminated adjacent to the nitro group144. Pteridines are converted into alkylarnino derivatives by the action of a solution of potassium permanganate in an alkylamine, e.g. equation 51145. 

Probtem 18.63 Synthesize from naphthalene and any other reagents (a) naphthionic acid (4-amino-l-naphthalenesulfonic acid), (b) 4-amino-l-naphthol, (c) 1,3-dinitronaphthalene, (d) 1,4-diaminonaphthalene, (e) 1,2-dinitronaphthalene. Do not repeat the synthesis of any compound. ... 

The first information (37JGU739 67CB2164) about the synthesis of 1,2-dihydrobenzo[crf]indazole by reduction of 1,8-dinitronaphthalene or naphtho[equilibrium with 1,3- and l,5-dihydrobenzo[c[Pg.43]

Dinitronaphthalene could be expected from the coulometric data [110] to undergo ring closure on reduction, but suitable conditions have not been found yet. The diamine [111] and 8-amino-5-hydroxy-l,4-naphthoquinone-1-imine [112] have been reported as products. 

Some kinds of proton sponges are best prepared starting from accessible l,8-bis(methyl-amino)naphthalene (4) or its derivatives2,40-43. For example, the optimal synthesis of l,8-bis(dimethylamino)-4,5-dinitronaphthalene (51) consists in methylation of compound 50, which in turn can be prepared from perimidone 49 (Scheme 2)44,45. 

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