Detail of "119-63-1"

Reference

Colored monoazo color couplers

Whitear, Brian Ronald David; Noxon, Raymond Geoffrey (Ciba-Geigy A.-G., Switz.). Brit. GB 1523937 6 Sep 1978, 11 pp. (English). (United Kingdom). CODEN: BRXXAA. CLASS: IC: C09B029-20; G03C007-34; C07C103-75; C07C149-32. APPLICATION: GB 75-39557 26 Sep 1975. DOCUMENT TYPE: Patent CA Section: 40 (Dyes, Fluorescent Whitening Agents, and Photosensitizers) Magenta cyan color couplers (I; R = H, halogen, alkoxy, dialkylamino, cyclic amino, alkylthio, arylthio, alkarylthio, aralkylthio, heterocyclylthio; R1 = alkyl or substituted alkyl; R2 = H , alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, substituted aryl; R3 = amino group contg. an oil-solubilizing ballasting group) for the prepn. of color-cor. photog. negs. were manufd. which absorb both blue and green light, act as masks for unwanted cyan dye absorption, and give a cyan dye when coupled with the oxidn. products of a p-phenylenediamine developer. Thus, 17.5 g 2-chloro-5-nitroaniline [6283-25-6], Ph 1-hydroxy-2-naphthoate [132-54-7], and 15 mL pyridine were distd. 15 min at 180° and 50 mL AcOH was added giving 26 g 1-hydroxy-2-naphth-(2-chloro-5-nitroanilide) [4036-91-3], 30 g of which was dissolved in 250 mL MeOH contg. 5 g LiOH. After hydrogenation at >1 atm using a Pd-C catalyst, 500 mL aq. AcOH was added and 26 g of the resulting 1-hydroxy-2-naphth-(5-amino-2-chloroanilide) [53411-20-4] was suspended in 300 mL boiling PhMe to which 29 g 2,4-di-tert-amylphenoxyacetyl chloride [88-34-6] was added. The mixt. was refluxed 17 h and evapd. yielding 40 g 1-hydroxy-2-naphth-[5-(2,4-di-tert-amylphenoxyacetylamino)-2-chloroani lide] (II) [70609-70-0]. To 15 mL HCl was added 4.1 g 4-amino-N-methylacetanilide [119-63-1] in 15 mL AcOH at 5° and the soln. was diazotized. Anhyd. KOAc (35 g) and 11 g II in 250 mL MeO(CH2)2OH were cooled to 10° and the diazonium soln. added. The mixt. was poured into H2O to give azo dye [70609-86-8] as a purple ppt. A photog. film was coated with a gelatin Ag halide emulsion layer contg. a high b.p. water-insol. org. oil former with the cyan color coupler and a noncolored cyan color coupler.

Localization of minor liver-bound metabolites of 3'-methyl-p-dimethylaminoazobenzene with anti-hapten antibodies

Localization of minor liver-bound metabolites of 3'-methyl-p-dimethylaminoazobenzene with anti-hapten antibodies. Carruthers, Christopher; Baumler, Alverna; Neilson, Ann (Orchard Park Lab., Roswell Park Mem. Inst., Buffalo, N. Y., USA). Cancer Res., 37(7, Pt. 1), 2099-104 (English) 1977. CODEN: CNREA8. DOCUMENT TYPE: Journal CA Section: 4 (Toxicology) The localization of known and possible metabolites of azocarcinogens such as p-amino-N,N-dimethylaniline [99-98-9], p-amino-N-monomethylaniline [623-09-6], and aniline [62-53-3] or aminobenzene [62-53-3] bound to components of liver cells of rats fed single or multiple doses of 3'-methyl-p-dimethylaminoazobenzene (I) [55-80-1] was detd. with the use of antibodies raised against p-azo-N,N-dimethylaniline (p-azo-DA), p-azo-N-monomethylaniline (p-azo-MA), and azoaniline (azo-B) in the indirect fluorescent antibody procedure. Antisera raised against p-azo-N-acetyl-N-methylaniline (p-azo-AMA) were also used since p-amino-N-acetyl-N-methylaniline (p-amino-AMA) [119-63-1] is a possible metabolite of I and is structurally related to the aniline derivs. examd. Antisera raised against p-azo-AMA not only reacted in agar with p-azo-AMA-ovalbumin conjugate, but also cross-reacted with p-azo-MA-ovalbumin conjugate. Anti-azo-B and anti-p-azo-MA antisera reacted in agar only with azo-B-ovalbumin and p-azo-MA-ovalbumin conjugates, resp. The p-azo-DA-ovalbumin conjugate did not react in agar with anti-p-azo-MA, anti-azo-B, or anti-p-azo-AMA antisera. Antisera raised against p-azo-AMA, azo-B, and p-azo-MA reacted in agar with the cytosol prepd. from the livers of rats treated with I or p-amino-AMA. When antisera raised against p-azo-DA, p-azo-MA, and azo-B were absorbed with cytosol from normal rat liver, these absorbed antisera reacted with liver cells from rats fed I. The antibodies responsible for this reaction were removed from the 3 antisera by absorption with cytosol from livers of rats fed I, and the antibodies were also removed from the anti-p-azo-MA antisera by absorption with cytosol from the livers of rats fed p-amino-AMA. When anti-p-azo-DA, anti-p-azo-MA, and anti-azo-B antisera were absorbed with the cytosol from normal rat liver, only anti-p-azo-MA antisera reacted with liver cells from rats fed p-amino-AMA, and the antibodies responsible for this reaction were removed from the antisera by absorption with cytosol from rats fed p-amino-AMA but not by absorption with cytosol from rats fed I. The antisera raised against p-azo-DA, p-azo-MA, or azo-B did not react with carcinoma cells induced in rat liver by I, but they did react with liver cells adjacent to the carcinomas still capable of binding I.