Nitro phenylacetic acid

In order to provide an optical fixing mechanism, p-nitro-phenylacetic acid can be used in the monomer mixture (44). It reduces the dye to the leuco state upon overall exposure to uv light from a mercury lamp. However, the color of the dye returns on standing, and this is only a temporary fixing mechanism because it does not polymerize all the remaining monomer. 

Oxidative degradation of substituted pyruvic acids is accomplished by treating an aqueous solution of the sodium salt with 30% hydrogen peroxide (Superoxol) at 0-15°. Good descriptions have been published for the preparations of o-hydroxyphenylacetic acid (34%), 3,4-dim.ethoxy-phenylacetic acid (60%), m-chlorophenylacetic acid (57%), and o-nitro-phenylacetic acid. ... 

Indole, CgHyN, is of interest on account of its relation to indigo (667) and the fact that it is the product of the decomposition of certain proteins. Syntheses of indole lead to the conclusion that it is made up of a benzene nucleus condensed with a pyrrole nucleus. When o-nitro-phenylacetic acid is reduced with tin and hydrochloric acid the amino-phenylacetic acid formed loses water spontaneously and passes into oxindole —... 

Deady et al. used methyl 2-amino-3-formylbenzoate with o-methoxy-and o-nitro-phenylacetic acids, phenylpyruvic acid, and benzo[fc]thio-phen-2-one to prepare quinoline analogs (99SC4223, 00AJC143). 

Also obtained by reaction of p-nitro-phenylacetic acid with resorcinol in the presence of boron trifluoride... 

The hydrochloride of 3-amino-4-hydrazinopyridine 65 was prepared by reaction of the 4-chloro-3-nitropyridine derivative with ethoxycarbonyl-hydrazine in phenol to give the hydrochloride of ethyl 3-(3-nitro-4-pyridyl)carbazate 64 (R2 = OEt), which on successive heating in concentrated hydrochloric acid and hydrogenation over Pd/C gave 65. Its reaction with phenylacetic acid or with phenoxyacetic acid gave the hydrochloride... 

It may be mentioned in passing that Chapman and coworkers148 determined rate coefficients for the reactions at 30 °C of phenylacetic acid and various meta- or /zara-substituted phenylacetic acids with DDM in 10 alcohols as solvents. The nitro acids were included. There were some interesting indications of solvent dependence for the apparent a values of /zara-substituents, including N02, for which values ranging from 0.69 to 0.77 were... 

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). 

A mixture of 30.2 g. (0.20 mole) of o-nitrobenzaldehyde,2 40 g. (0.29 mole) of phenylacetic acid, 100 ml. (1.08 moles) of acetic anhydride, and 20 g. (0.20 mole) of triethylamine is refluxed for 15 minutes in a 500-ml. flask. The solution is cooled to 90°, and 100 ml. of cold water is added over a 5-minute period at a rate that maintains the temperature above 90° (Note 1). The solution is filtered at 95-100° and cooled to 20°. frims-o-Nitro-a-phenylcinnamic acid precipitates in the form of light-orange crystals. It is separated by filtration and washed with 60 ml. of 50% acetic acid and with water. The dried acid weighs 39-42 g. (72-77%) and melts at 195-198°, which corresponds to a purity of about 98% (Note 2). After recrystallization from 500 ml. of toluene, it is in the form of yellow prisms weighing 38-39 g. (71-72%) and melting at 197.8-198.3°. 

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

The relation between the constant of the para acid and that of the ortho or meta acid varies with the nature of the substituent. While p-nitrobenzoic acid is a slightly stronger acid than m-nitro-benzoic acid, the constant of p-chlorobenzoic acid is only about one-half that of the meta acid. The case of p-hydroxybenzoic acid is a striking one while o-hydroxybenzoic acid and m-hy-droxybenzoic acid are more highly ionized than benzoic acid, the constant of the para acid is less than half that of benzoic acid. A satisfactory explanation of such facts as these would, no doubt, materially advance organic chemistry. The effect of a phenyl radical on a carboxyl group in a side-chain, is shown by the constants for phenylacetic acid, hydrocinnamic acid, and cinnamic acid. 

Aromatic tt or / values derived from meta and para substituents tend to be identical, but ortho substituents often give outlying values, e.g., when they permit internal hydrogen-bonding, lipophilicity is increased. Nevertheless, by much more complicated calculations, Fujita and Nishioka (1975) have made a special table for ortho substituents that integrate well with the meta and para values. Apart from this, these tt and / values are very sensitive to polar environments. For example, tt for chlorine substituted in benzene is 0.71, but this becomes (insertion is in all cases, meta) 0.61 in nitrobenzene, 0.68 in phenylacetic acid, 0.83 in benzoic acid (all ionizable substances are corrected for ionization), 0.98 in aniline, and 1.04 in phenol. This difference of 0.43 between extremes is increased to 0.90 when nitro-group replaces chlorine in the... 

A number of reactants that can give rise to anionic species have been used. These include esters of phenylacetic acid/ malonic and alkymalonic acids/ " acetoacetic acid/ etc. Also useful are some nitriles and nitro-alkanes. The case of 2-nitropropane 76 is interesting. Kloetzel reported that the nature of the product from diethyl fumarate depends on the amount of diethylamine (DEA) catalyst employed. Thus, using 0.20 mole of catalyst, the simple addition product 77 was formed in a 90% yield. However, with 1.25 moles of base, elimination occurred giving 78 in an 83% yield. 

Hammett found, for example, that the nitro group has a stabilising effect on other dissociation reactions such as those of phenylacetic acid. He then proposed a quantitative relationship to account for such findings... 

In the Pschorr synthesis (Scheme 12.12), a Perkin reaction (see Chapter 6) between 2-nitrobenzaldehyde and sodium phenylacetate in the presence of acetic anhydride yields 3-(2-nitrophenyl)-2-phenyl-propenoic acid. Reduction of the nitro group and deamination of the resulting amine via its diazonium salt (see Chapter 8) is accompanied by cyclization. Thermal decarboxylation completes the sequence. 

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