Phenylacetic acid nitration

Inclusion of basic nitrogen in the p-position is also compatible with antiinflammatory activity in this series. Nitration of phenylacetic acid (27) affords 28. Methyl iodide alkylation of the enolate prepared from 28 using two equivalents of sodium hydride gives 29. This appears to involve an Ivanov intermediate (28a). Catalytic reduction of the... 

Nitrophenylacetic acid has been formed by the nitration of phenylacetic acid 1 by the hydrolysis of its ester 2 or its amid 3 and by the hydrolysis of its nitrile with hydrochloric acid.4... 

Organic aerosols formed by gas-phase photochemical reactions of hydrocarbons, ozone, and nitrogen oxides have been identified recently in both urban and rural atmospheres. Aliphatic organic nitrates, such dicarboxylic acids as adipic and glutaric acids, carboxylic acids derived from aromatic hydrocarbons (benzoic and phenylacetic acids) and from terpenes emitted by vegetation, such as pinonic acid from a pinene, have been identified. The most important contribution in this held has been that of Schuetzle et al., who used computer-controlled... 

Methylcryptaustoline iodide (14) was synthesized from phenylacetic acid 47 by Elliott (39) as shown in Scheme 7. Nitration of 47 to the 6-nitro compound 48 and reduction with sodium borohydride afforded lactone 49. Reduction of the aromatic nitro group with iron powder in acetic acid gave ami-nolactone 50, which was converted to tetracyclic lactam 51 with trifluoroacetic acid in dichloromethane. Reduction of the lactam by a borane-THF complex followed by treatment with methyl iodide afforded ( )-0-methylcryptaustoline iodide (14). 

Naphthaline Naphthylamine -Sodium nitrate -Nitro naphthaline Phenylacetic acid Phosphorus Mercury-Sulphur... 

The condensation of dianions of ring-methoxylated phenylacetic acids like (10) with methyl nitrate provides a general, one-step procedure to the corresponding phenylnitromethane (11 equation 5)." Methods for the preparation of nitroacetic esters have been summarized. ... 

Fuming hydrobromic acid converts it into a-bromophenyl-acetic acid CeHs.CHBr.COOH, and hydriodic acid and red phosphorus into phenylacetic acid, C6H6.CH2.COOH. The acid cannot be nitrated, as concentrated nitric acid oxidizes it to benzaldehyde. 

Nitrosophenylhydroxylamine ammonium salt Nonylphenol Nuarimol 2-n-Octyl-4-lsothlazolin-3-one Oleyl hydroxyethyl imidazoline Paraformaldehyde Pentachlorophenol Phenoxyacetic acid Phenylacetic acid Phenylmercuric borate Phenylmercuric nitrate Phenylmercuric oleate p-Phenylphenol Phthalimide... 

Baeyer nitrated phenylacetic acid, and reduced this to o-aminophenylacetic acid, which lost water to form oxindole. By reducing nitroso-oxindole (prepared by Baeyer and Knop) to amino-oxindole, and oxidising this, Baeyer obtained isatin ... 

Under similar conditions, alkyl esters of phenylacetic acid were also easily nitrated to give a high proportion of the ortho isomers in good yields [27] ... 

Oxalic and malonic acids, as well as a-hydroxy acids, easily react with cerium(IV) salts (Sheldon and Kochi, 1968). Simple alkanoic acids are much more resistant to attack by cerium(IV) salts. However, silver(I) salts catalyze the thermal decarboxylation of alkanoic acids by ammonium hexanitratocerate(IV) (Nagori et al., 1981). Cerium(IV) carboxylates can be decomposed by either a thermal or a photochemical reaction (Sheldon and Kochi, 1968). Alkyl radicals are released by the decarboxylation reaction, which yields alkanes, alkenes, esters and carbon dioxide. The oxidation of substituted benzilic acids by cerium(IV) salts affords the corresponding benzilic acids in quantitative yield (scheme 19) (Hanna and Sarac, 1977). Trahanovsky and coworkers reported that phenylacetic acid is decarboxylated by reaction with ammonium hexanitratocerate(IV) in aqueous acetonitrile containing nitric acid (Trahanovsky et al., 1974). The reaction products are benzyl alcohol, benzaldehyde, benzyl nitrate and carbon dioxide. The reaction is also applicable to substituted phenylacetic acids. The decarboxylation is a one-electron process and radicals are formed as intermediates. The rate-determining step is the decomposition of the phenylacetic acid/cerium(IV) complex into a benzyl radical and carbon dioxide. 

Silver fluoborate, reaction with ethyl bromide in ether, 46, 114 Silver nitrate, complexing with phenyl-acetylene, 46, 40 Silver oxide, 46, 83 Silver thiocyanate, 45, 71 Sodium amide, in alkylation of ethyl phenylacetate w ith (2-bromo-ethyl)benzene, 47, 72 in condensation of 2,4-pentanedione and 1 bromobutane to give 2,4-nonanedione, 47, 92 Sodium 2 ammobenzenesulfinate, from reduction of 2 mtrobenzenesul-finic acid, 47, 5... 

Alkaline nitration with alkoxide bases and nitrate esters was first explored by Endres and Wislicenus who synthesized phenylnitromethane by treating ethyl phenylacetate with potassium ethoxide in ethanol, followed by addition of ethyl nitrate and hydrolysis-decarboxylation of the resulting a-nitroester with aqueous acid. Phenylnitromethane is synthesized in a similar way via alkaline nitration of benzyl cyanide, followed by treatment of the resulting a -nitronitrile with aqueous base. ° Wieland and co-workers used alkali metal alkoxides and nitrate esters for the nitration of cyclic ketones but the yields and purity of product are often poor. ° ... 

Acetophenones - methyl phenylacetates, ArCOCH3 -- ArCH2COOCH, Treatment of an acetophenone with thallium(Ill) nitrate in methanol containing a trace of perchloric acid at room temperature for 2-18 hr. results in formation of a methyl arylacetate in 60-95 % yield. The mechanism suggested for this transformation is shown in the formulation. The reaction provides an alternative to the Willgerodt-Kindler reaction."... 

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