1- Bromo-2-naphthylamine

Oscillation photographs showed no intermediate layer lines when the following guests were used nitrobenzene, l-chloro-3-bromo-benzene, m-xylene, 1,2,3,4-tetrahydroquinoline, azulene, 1-bromo-2-naphthylamine, biphenyl, p-toluidine, 9,10-dihydroanthracene, phenanthrene, pyrene 3. All complexes have the composition 4 1 except for the picene complex where this ratio is 8 1. 

Tetran itro- 1-am i non aphth a I ene(Calle d by Merz, a-Tetranitro-l-naphthylamine), It yel ndls, mp 194°. Was first prepd by Merz Weith by treating 4-bromo-l,3,6,8-tetranitro-naphthalene in benzene with NHs(Ref 2). Another method is to heat the corresponding tetranitro-halogen compd with urea at atm pressure, using xylene as a diluent(Ref 3) This compd is expl... 

The iV-methylamine (160) (R = Me) gives a complex mixture of products when treated under the same conditions.186 It was shown subsequently that prior reduction of the anils used as starting materials is, in fact, unnecessary since in the presence of potassamide in liquid ammonia (o-chlorobenzylidene)aniline forms phenanthridine in excellent yield, and the analogous anils from p-toluidine and a-naphthylamine undergo ring closure under similar conditions. In view of the known trans geometry of the anils and the unlikelihood of trans-cis equilibration under these conditions this reaction deserves further study.187 Potassamide in liquid ammonia also converts 2-bromo-iV-ethyl-3 -hydroxybenzanilide (162) into a mixture of iV-ethyl-3-(164) and N-ethyl-1 -hydroxyphenanthridone (165), probably via the aryne (163).188... 

Both, benzo[e] indole and benzo[g]indole can be obtained by the reaction of l-bromo-2-naphthylamine or 2-bromo-l-naphthylamine with CH2COPh in DMSO [61], and CH2COBu-t and CH2COCH(OMe)2 anions in liquid ammonia in variable yields (46-82%) [62]. In addition to this, the photostimulated reaction of vie aminohalo pyridines with the anion of CH2COBu-t or CH2COMe ions leads to azaindoles in high yields (75-95%) [63]. 

This product results when phenyl-)3-naphthylamine is used in the general method, or by reduction of 2-j8-naphthylaminopbenylarsinic acid. It crystallises from sym.-tetrachloroethane in ydlow needles, M.pt. 249° to 250 C. The corresponding 12-bromo-derivaiive is obtained by reducing 7 12-benzophenarsazinic acid in alcoholic hydrobromic acid. It forms short, deep, orange-coloured needles, M.pt. 251 to 252° C., with decomposition. 

Tefranitro l-aminonapMhalene( Called by Merz, S-Tetranitro-naphthylamine). Vel ndls, mp 202°. Was obtained by Merz Weith by moderately warming 4-bromo-l,3,5,8-tetranitronaphthalene(suspended in benzene) with NHj(Ref 2). This compd is a mild expl... 

Using 02 Anderson et al. showed that the two major phenolic metabolites of N-phenyl-2-naphthylamine produced by liver enzymes are likely to be derived via arene oxide intermediates. The mechanism by which bromo-benzene is converted to 4-bromocatechol in isolated rat hepatocytes was shown with 62 to proceed via dehydrogenation of a dihydrodiol intermediate rather than by two successive hydroxylation reactions of the substrate. Similar studies have been performed on chlorpromazine. 

Pale yellow needles. M.p. 131-2°. Sol EtOH, EtjO. Sublimes. Zn + AcOH — 4-bromo-2-naphthylamine. ... 

Nitro-2-naphthylamine in chloroform treated at room temp, with a soln. of bromine in chloroform, the resulting hydrobromide collected after 24 hrs., washed with chloroform, which is then removed in vacuo, the product suspended in ice-water and treated with aq. NH3 l-bromo-3-nitro-2-naphthylamine. Y 95%.—This is an excellent preparative method. The amines are readily soluble in the cold solvent the HBr liberated forms the insoluble hydrobromide of most of the product. This can be removed by filtration, usually in high yield, and invariably in a high state of purity since non-basic by-products re-... 

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