Naphthol Naphthyl amine

A. Matsuzaki, S. Nagakura, and K. Yoshihara, Interactions of /1-naphthol and -naphthyl-amine in their excited singlet states with triethylamine, Bull. Chem. Soc. Jpn. 47, 1152-1157 (1974). 

The nitrobenzene solution, together with the suspended solid material, is shaken with a mixture of 300 cc. water and 100 grams of ice, then twice with 100-cc. portions of cold water. The combined aqueous extracts are filtered through a moistened paper and then saturated with 200 grams of salt, whereupon sodium 2-naphthol-l-sulfonate is precipitated in colorless plates. Stirring is continued until all of the salt is dissolved, and the mixture is allowed to stand overnight, then filtered. The product is pressed out and washed twice with saturated salt solution. The filter cake is used directly for the preparation of 2-naphthyl-amine-l-sulfonic acid after tests have shown that it does not fluoresce in soda solution and does not yield a water soluble, orange red dye with diazotized aniline and thus does not contain isomeric naphtholsul-fonic acids. 

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. ... 

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 ... 

Note Note that the diazotization of primary aromatic amines can also be achieved by placing the chromatogram for 3 — 5 min in a twin-trough chamber containing nitrous fumes (fume cupboard ). The fumes are produced in the empty trough of the chamber by addition of 25% hydrochloric acid to a 20% sodium nitrite solution [2, 4], iV-(l-Naphthyl)ethylenediamine can be replaced in the reagent by a- or -naphthol [10, 14], but this reduces the sensitivity of detection [2]. Spray solutions Ila and lib can also be used as dipping solutions. 

Diazotization of the primary amine [3, 17] followed by coupling with a-naphthol or N-(l-naphthyl)-ethylenediamine. Sulfonamides also react [18]. 

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 applications of re-acidic chiral stationary phases include the resolution of a-blockers and /1-blockers, amines, arylacetamine, alkylcarbinols, hydantoins, barbiturates, naphthols, benzodiazapines, carboxylic acids, lactams, lactones, phthaldehydes selenoids, and phosphorus compounds. Hyun et al. [16] achieved a chiral resolution of a homologous series of iV-acyl-x-(l-naphthyl )cthylaminc on AA(3,5-dinitrobenzoyl-(i )-phenylglycine and N-(3,5 - dini tr o ben zoy I)-(,S ) -1 c u c ine CSPs. The authors used hexane-2-propanol (80 20, v/v) as the mobile phase. Similarly, the scope of re-basic CSPs comprises the chiral resolution of / -blockers, amino acids, amines, diamines, amino phosphonates, naphthols, benza-diazapines, carboxylic acids, hydroxy acids, dipeptides, tripeptides, diols,... 

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