4-aminophenyl-2-ethanol

The reactant corresponding to retrosynthetic path b in Scheme 2.2 can be obtained by Meerwein arylation of vinyl acetate with o-nitrophcnyldiazonium ions[9], Retrosynthetic path c involves oxidation of a 2-(o-nitrophenyl)ethanol. This transformation has also been realized for 2-(o-aminophenyl)ethanols. For the latter reaction the best catalyst is Ru(PPhj)2Cl2. The reaction proceeds with evolution of hydrogen and has been shown to be applicable to a variety of ring-substituted 2-(o-aminophenyl)ethanols[10]. 

Note No other nitrated derivs of aminophenyl-ethanols were found in Beil or CA through 1956 [Cf with j8-(2,4,6-Trinitronitranilino)-ethanol Nitrate described under Anilinoethanol]... 

Ethanolaniline. See under Aminophenyl-ethanol and under Anilinoethanol A245-R A424-L... 

Aromatic nitro alcohols are converted by hydrogenationor by the action of metals and acids. Various combinations have been compared in the preparation of /3-(4-aminophenyl)-ethanol. ... 

In an interesting synthesis of 2-cyano-4,5-dihydro-3//-3,l-benzoxazepine 68 Besson el al. have found that reaction of 2-(aminophenyl)ethanol reacts with 4,5-dichloro-1,2,3-dithiazolium chloride to form a SchifFs base, the anion of which 66 undergoes rearrangement to form the above compound in a Smiles rearrangement involving the formation of the spiro-intermediate 67 (Scheme 7) <97SL704>. 

Fig. 1. Synthesis of A -(2-p-azidophenylethyl-l,l- Hs)norlevorphanol (APL) [J. I-DeGraw and J. S. Engstrom, J. Labelled Compd. 11, 233 (1975)]. Compounds (I) methyl-p-aminophenylacetate (II) 2-(p-aminophenyl)ethanol-(l,l- Hi) (III) 2-(p-azidophenyl)ethanol-(l.l- Hs) (IV) 2-(p-azidophenyl)ethanol-(l,l- H2)-p-toluene-sulfonate (V) norlevorphanol (VI) V-(2-p-azidophenylethyl-l,l- H2)norlevor-phanol, [ H]APL.

The technique of using templates during the polymerization of phenols, thiols, and anilines was also used successfully to produce imprinted polymers. Besides phenol, various other monomers (p-substituted phenols, aniline, 4-aminophenyl ethanol, and thiol) were polymerized in buffer solution in the presence of Cu(II), Ni(II), or Fe(III). The corresponding polymers displayed selectivity in binding to the metal, which was used in the imprinting step against the other three metals used for the screening [106]. It has... 

Peris and coworkers reported on a Ir/P-bimetallic complex having a 1,2,4-trimethyltriazolylidene ligand act as an efficient catalyst for the tandem oxidative cyclization of 2-(orf/zo-aminopheny)ethanol to afford indole derivatives [164]. In a typical example, 2-(ort/zo-aminophenyl)ethanol (1 equiv.) was reacted in the... 

Acylation. Reaction conditions employed to acylate an aminophenol (using acetic anhydride in alkaU or pyridine, acetyl chloride and pyridine in toluene, or ketene in ethanol) usually lead to involvement of the amino function. If an excess of reagent is used, however, especially with 2-aminophenol, 0,A/-diacylated products are formed. Aminophenol carboxylates (0-acylated aminophenols) normally are prepared by the reduction of the corresponding nitrophenyl carboxylates, which is of particular importance with the 4-aminophenol derivatives. A migration of the acyl group from the O to the N position is known to occur for some 2- and 4-aminophenol acylated products. Whereas ethyl 4-aminophenyl carbonate is relatively stable in dilute acid, the 2-derivative has been shown to rearrange slowly to give ethyl 2-hydroxyphenyl carbamate [35580-89-3] (26). 

A mixture of 7.8 grams (0.05 mol) of )3-(p-aminophenyl)ethyl chloride hydrochloride, 12.5 grams (0.025 mol) of 4-phenyl-4-carboethoxypiperidine carbonate, 10.5 grams (0.125 mol) sodium bicarbonate, and 100 cc of anhydrous ethanol are mixed, stirred and heated under reflux for a period of approximately 40 hours and then concentrated in vacuo to dryness. The residual material is triturated with 50 cc of water, decanted, washed by decantation with an additional 50 cc of water, and then dried in vacuo to give N-[)3-(p-aminophenyl)-ethyl] -4-phenyl-4-carboethoxypiperidine. 

The N-[)3-(p-aminophenyl)ethyl]-4-phenyl-4-carboethoxypiperidine is dissolved in 50 cc of hot anhydrous ethanol, an excess (about 20 cc) of 20% alcoholic hydrochloric acid solution is added upon scratching the side of the container crystals form. One hundred cubic centimeters of ether are then added to the mixture, the ethereal mixture is cooled, and the crystalline material which precipitates is recovered by filtration, washed with ether, and dried to give 12.7 grams of N-[)3-(p-aminophenyl)ethyl]-4-phenyl-4-carboethoxypiperidine dihydrochloride which can be further purified by recrystallization from ethanol or methanol to give substantially pure material MP 275°-277°C. 

Preparation of model compounds and polyurethanes. A procedure for the preparation of the non-silicon containing monocarbamate and biscarbamate models has been reported previously (8). In order to obtain the silicon containing model compound, 5.0 g of bis(4-aminophenyl) dimethyl silane [synthesized according to Pratt, et.al (9)] was added to 7.0 g ethyl chloroformate at room temperature. A salt immediately formed. The mixture was refluxed for 15 min. The solution was then cooled, vacuum filtered, and recrystallized from ethanol to yield 1.0 g of a white powder MP 162-3 °C Anal. c20H26°4N2Si Calc. C, 62.17 H, 6.70 N, 7.23 Found C, 62.01 H, 6.79 N, 7.42. 

The template condensation of diethyl jV-(2-aminophenyl)aminomethy-lenemalonate (162, R = H), ethyl 2-[)V-(2-aminophenyl)amino]methy-leneacetoacetate, and Ni(II) acetate tetrahydrate in boiling ethanol for 20 hr gave a 60% yield of unsymmetrically substituted nickel(II) complexes of type 1595, which were characterized by UV, H- and, 3C-NMR spectra (88MI2). 

The application of diazo coupling is somewhat limited by the availability of the p-aminophenyl glycosides, particularly of those of the oligosaccharides. Their precursors, the p-nitrophenyl glycosides, are usually obtained by the condensation of a per-O-acetylated glycosyl halide with p-nitrophenol in ethanol (Michael reaction)19,20 or by the reaction of a per-O-acetylated sugar with p-nitrophenol in the presence of a Lewis acid catalyst (Helferich reaction).21 p-Nitrobenzyl 1-thioglycosides have also been prepared by the condensation of the... 

Buffer catalysis of the hydrolysis of phenyl (311 R = Ph) and methyl (311 R = Me) benzenesulfinates to give the sulfinic acid (312) and alcohol ROH is strongly accelerated by both carboxylate and amine components of the buffer which give Bronsted /i values of approximately unity on separate lines. The carboxylates are about 44 tunes more effective than amines of similar basicity. A concerted. S n2 mechanism with a hypervalent intermediate (313) is proposed for the nucleophilic reaction of these esters.286 The reaction of the thiosulfinate esters (314) with sulfenyl chlorides RSCI and sulfenate esters (315) to give sulfinyl chlorides and disulfides and sulfinate esters and disulfides, respectively, has been studied.287 Hydrolysis of 2-(3-aminophenyl)sulfonyl-ethanol hydrogensulfate gives under different conditions various products such as the ether (316) and the sulfone (317).288... 

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