4-Methoxy-1 -naphthylamine, reaction

The use of trialkyl phosphates for dialkylation of anilines has been found applicable to naphthylamines and to a large number of anilines substituted in the ortho, meta, or para position by groups such as chloro, methoxy, and methyl and in the meta position by fluoroalkyl (author s laboratory). The reaction has been used to introduce ethyl and M-butyl as well as methyl groups by employing the appropriate phosphate esters. The reported yields range from 50% to 95%. 

Arylnaphthalenes. Arylnaphthalenes can be prepared by replacement of the amino group of naphthylamines by aryl groups. a-Phenyl-naphthalene can be prepared satisfactorily only through the stabilized diazonium salt method, but /3-phenylnaphthalene is obtained readily by several procedures. A considerable number of derivatives of /3-phenylnaphthalene have been prepared. An example is 5-nitro-6-methoxy-2-phenylnaphthalene (XII), which can be obtained in 19% yield from the nitromethoxy-/3-naphthylamine and benzene. From the reaction between diazotized /S-naphthylamine and nitrobenzene and sodium acetate, /S-(2-nitrophenyl)-naphthalene (XIII 14%) and /3-(4-nitrophenyl)-naphthalene (XIV 26%) are formed. 

The electron-cytochemical method for localization of DPP was optimized by Lojda (1981) and its modification for cytochemical reaction for DPP in glutaraldehyde prefixed yeast cells was described recently (Voffsek in preparation). In principle, the synthetic dipeptide substrate has its carboxyl terminus bound to 4-methoxy-2-naphthylamine. The primary reaction product was formed by coupling hexazonium pararosaniline (HPR) with the MNA liberated by DPP and was osmiophilic. Thus postfixation by osmium tetrox-ide revealed also the electron-dense final reaction product on the background of the general osmiophilia of the matrix phase and membranes. 

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