Amines, naphthyl, from naphthols

Bucherer Reaction. The reversible conversion of a naphthylamine to a naphthol in the presence of an aqueous sulfite or bisulfite is valuable in the synthesis of naphthalene dye intermediates. It is used in the preparation of naphthols from naphthylamine or is employed for the reverse transformation—naphthyl-amines from naphthols ... 

The rare example of synergistic action of a binary mixture of 1-naphthyl-A-phcnylaminc and phenol (1-naphthol, 2-(l,l-dimethylethyl)hydroquinone) on the initiated oxidation of cholesterol esters was evidenced by Vardanyan [34]. The mixture of two antioxidants was proved to terminate more chains than both inhibitors can do separately ( > /[xj). For example, 1-naphtol in a concentration of 5 x 10 5 mol L-1 creates the induction period t=170s, 1 -naphthyl-A-phenylamine in a concentration of 1.0 x 10-4 mol L 1 creates the induction period t = 400s, and together both antioxidants create the induction period r = 770 s (oxidation of ester of pelargonic acid cholesterol at 7= 348 K with AIBN as initiator). Hence, the ratio fs/ZfjXi was found equal to 2.78. The formation of an efficient intermediate inhibitor as a result of interaction of intermediate free radicals formed from phenol and amine was postulated. This inhibitor was proved to be produced by the interaction of oxidation products of phenol and amine. 

The sulfonic acids of naphthalene, of the naphthols, and of the naphthyl-amines are of great importance as intermediates, for azo and triphenyl-methane dyes. In view of the complexity and the specialized nature of this field, it will be considered here only very briefly and from the standpoint of general principles. 

Yellow needles from hot EtOH or CHCL. M.p, 137-5° (132°). Spar, sol. Et,0, EtOH, CgHg. Prac. insol, H5O. Non-volatile in steam. Sn -J- HCl —>- 2 4-manuno-l-naphthol. Ale. NHj at 200° —> 2 4-dinitro-l-naphthyl-amine. Na salt is the dyestuff Martius Yellow. 

Victor Merz (Odessa, 12 December 1839-Ziirich, 25 May 1904) was associate professor (1869) and professor (1871) in the university of Zurich. He worked first on inorganic chemistry. He synthesised ketones from acid chlorides and hydrocarbons, sodium formate from carbon monoxide, and oxalic acid by heating alkali formates. He prepared aromatic carboxylic acids by distilling sulphonates with potassium cyanide and hydrolysing the nitriles produced, discovered a- and j8-naphthoic acids, and prepared j8-naphthyl-amine from j8-naphthol by the action of ammonia and zinc chloride. ... 

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