4’-Hydroxy acetanilide

Roberts, S.A., Veronica, F.P. and Jollow, D.J. (1990) Acetaminophen structure-toxicity studies In vitro covalent binding of a non-hepatotoxic analog, 3-hydroxy-acetanilide. Toxicology and Applied Pharmacology, 105, 195-208. 

AA and IAA simultaneously Fortified fruit juice Metaphosphoric acid (2.5%) extraction add 4 -hydroxy-acetanilide as internal standard Analytical Spherisorb ODS (250 X 4 mm, 5 ytzm Waters ). 

Figure 9.121 HPLC chromatogram of 4-hydroxy-, 3-hydroxy-, and 2-hydroxy acetanilide and acetanilide. About 12.5 fig of each of the four compounds in a total volume of 25 f L of methanol was injected. Approximately 0.33 mL fractions were collected. (From Guenthner et al 1979.)...

Depletion of cellular substrates involved in activation of carcinogens can result in Inhibition of carcinogenicity (35-37). In these studies, it was shown that acetanilide decreased the liver carcinogenicity of 2-acetyl aminofluorine (2-AAF) by decreasing the formation of the ultimate carcinogenic metabolite, the sulfate ester of 2-AAF, mainly through depletion of the available sulfate as a result of sulfation of p-hydroxy acetanilide (36,37). 

Aminophenol is obtained by treating aniline with sulphuric acid and potassium hydroxide, which on acetylation with acetic anhydride yields the />-hydroxy acetanilide. The resulting product on ethylation with ethyl bromide forms phenacetin. 

Another interesting case of carbo-spirocyclization of phenolic substrates is that reported by Chabaud and GuUlou on the conversion of para-hydroxy acetanilides of type 133 into 1,2-aza/carbo-dispirodienones 134, using BTI in TFE at 0°C (Fig. 34) [92]. This is the first example of a synthesis of 1,2-dispirodienones via a X -iodane-mediated phenol dearomatization. 

Me ether see 4 Methoxyaniline, M-00073 Et ether see 4-Ethoxy aniline, E-0005I N- c.- [103-90-2]. 4-Hydroxy acetanilide. 4-Acetamidophenol. F -(4 Hydroxyphenyl)acetamide. Acetaminophen, USAN. Paracetamol, BAN, INN. Panadol. Tramil. Hedex. Numerous proprietary names CgHpNOj M 151.165... 

Udenfriend et al. observed that aromatic compounds are hydroxyl-ated by a system consisting of ferrous ion, EDTA, ascorbic acid, and oxygend Aromatic and heteroaroinatic compounds are hydroxylated at the positions which are normally most reactive in electrophilic substitutions. For example, acetanilide gives rise exclusively to the o-and p-hydroxy isomers whereas quinoline gives the 3-hydroxy prod-uct. - The products of the reaction of this system w ith heterocyclic compounds are shown in Table XIII. 

Entsprechend wird 4-Hydroxy-N-benzyliden-anilin durch Essigsaure in 4-Hydroxy-N-benzyl-acetanilid (88% d.Th.) iiberfiihrt. 

Diethyl disulfide, see Phorate Diethyl dithiophosphate, see Phorate Diethyl ethylthiosuccinate, see Malathion Diethylfonmmide, see Dimethylamine. Triethylamine Diethyl fumarate, see Malathion cis-Diethyl fumarate, see Malathion irans-Diethyl fumarate, see Malathion Diethylhydroxylamine, see Triethylamine 2, 6 -Diethyl-2-hydroxy-N-(methoxymethyl)acetanilide, see Alachlor... 

Diloxanide furoate is the furoate ester of 2,3-dichloro-4-hydroxy-A-methyl acetanilide. This antiamoebic drug was developed as a result of the discovery that various a,a-dichloroacetamides possessed an amoebicidal activity [1]. Diloxanide furoate is considered as a safe and effective drug for the treatment of asymptotic or mildly symptomatic persons who are passing cysts of Entameba histolytica [2,3], It acts principally in the bowel lumen, and is used in the treatment of the intestinal amoebiasis. It is less effective in amebic dysentery than in asymptotic infection, but the furoate gives high intestinal concentrations and is possibly more effective than metronidazole in the treatment of cyst passers [4],... 

To a stirred slurry of 63.47 g (0.177 mole) of 3 -[(2-imino-3-thiazolidinyl) acetyl]acetanilide hydrobromide in 1 L of 95% ethanol, maintained at 5°C, is added 5.70 g (0.15 mole) of sodium borohyride. After stirring 40 min an additional 4.10 g of sodium borohydride is added and the mixture is acidified with hydrochloric acid and evaporated under reduced pressure. The residue is partitioned between chloroform and dilute aqueous ammonium hydroxide. Two further chloroform extracts are combined with the original, washed with brine, dried (sodium sulfate) and evaporated to give an oil. Treatment with acetone gives 6.77 g (48%) of 3 -[l-hydroxy-2-(2-imino-3-... 

Addition of 5.00 g (0.0158 mole) of 3 -[l-hydroxy-2-(2-imino-3-thiazolidinyl)ethyl]acetanilide hydrochloride to 15 ml of concentrated sulfuric icid is carried out in small increments over 0.5 h. The orange solution is stirred an additional 1 h, poured onto ice and made basic with concentrated ammonium hydroxide. The aqueous base is extracted twice with chloroform and the combined organic layers washed with water, brine, dried (sodium sulfate) and evaporated at reduced pressure to give 3.32 g (80% crude yield) of the 3 -(2,3,5,6-tetrahydroimidazo[2,l-b]thiazol-6-yl)acetanilide, melting point 164-166°C (recrystallization from 2-propanol). 

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