Nitro, acids phenyl acetic acid

The migration aptitudes in the reaction of ketones with peracetic acid in acetic acid as a solvent are in the order -anisyl > phenyl > >-nitro-phenyl.82 Cyclohexyl and phenyl are about equal in migration aptitude... 

The nitration of dimethyl (Af-phenyl-Ar-methylamino)methylthiomethy-lenemalonate with nitric acid in acetic acid at room temperature for 24 hr gave the 4-nitro derivative (1577) in 38% yield (69T4649). 

Cohare and co-workers reported that aristolactam BU (22) was prepared, following Kupchen s method, by Perkin condensation of 6-bromo-3,4-di-methoxy phenyl acetic acid (119) and o-nitrobenzaldehyde (120) (Scheme 14). The 2-bromo-4,5-dimethoxy-2 -nitro-ds-stilbene-a-carboxylic acid (121) was obtained. The nitro group of 121 was reduced with ferrous sulfate and ammonium hydroxide, and the resulting 2-bromo-4,5-dimethoxy-2 -amino-cw-stilbene-a-carboxylic acid (122) without purification was submitted to the Pschorr phenanthrene synthesis to yield l-bromo-3,4-dimethoxyphen-anthrene-lO-carboxylic acid (123). The phenanthrylamine 124 was prepared from 123 via a Schmidt reaction, and, by treatment with n-butyllithium and CO2, 124, afforded 22 (42). 

Nitration of benzo[6]furan may be achieved with nitric acid in acetic acid and affords the 2-nitro compound, although nitrogen dioxide in benzene is reported to give the 3-nitro compound. 2-Phenylbenzo[6]furan with nitric acid in acetic acid yields the 3- and 6-nitro compounds. Treatment of 2-bromobenzo[6]furan with nitric acid and sodium nitrite yields 2-nitrobenzo[6]furan. The only electrophilic substitution reported with a benzo[c]furan is nitration of 1,3-diphenylbenzo[c ]furan with sodium nitrate and sulfuric acid, and this occurs on a phenyl group. 

H0.N CH.CgH3(N02).N( N).Cl mw 228.60, N 24.51% pink ndls, mp stable at 60-80° but expl on strong heating. Can be prepd from 2-nitro-4-amino-phenyl acetic acid in cold coned HC1 by reaction with amyl nitrite. On heating with ale, this eompd forms 2-nitrobenzaldehyde-anti-oxime(qv)... 

Nitro-2-phenylindoles are obtained by electrophilic ipso-nitration of arylazo, hydroxymethyl, and acyl groups on treatment with two equivalents of 70% nitric acid in acetic acid at 25°C. No attack on the phenyl ring is observed under these conditions [80MI1 81JCS(P2)628]. Indolenines undergo nitration mainly at the 5-position (77-85%) (64TL803). 

Nitro-phenyl)-acetic acid methyl ester (24)... 

To a solution of (4-nitro-phenyl)-acetic acid methyl ester 24 (8.11 g, 41.6 mmol) in ethanol (208 mL) was added 10% Pd/C (3.20 g) and NH4HCOO (14.0 g in 10 equal portions every 5 min) while stirring at room temperature. The reaction was stirred for 24 h, followed by... 

Oxindole.—When ortho-nitro phenyl acetic acid is reduced to the ortho-amino phenyl acetic acid, the latter, being a gawwa-amino acid, loses water yielding a lactam which is known as oxindole. 

From ortho-Nitro Phenyl Acetic Acid.—Several other syntheses were developed by Baeyer. Starting with ortho-nitro phenyl acetic. CH2—COOH (i)... 

Several enzyme-linked immunosorbent assays (ELISAS) have been developed for trinitrotoluene, trinitrobenzene, 2,4-dinitrotoluene, and 2,6-dinitrotoluene using polyclonal antibodies raised in New Zealand white rabbits. Nitro substituted benzoic and phenyl acetic acids were used as haptens by conversion to the correspond NHS esters followed by coupling to protein carriers.The antibodies which were developed to 1,3-dinitroaromatic haptens had the greatest specificity and sensitivity when the nitroaromatic analytes contained a 1,3-dinitro functionality. In one ELISA system a lower detection limit for various 1,3-dinitroaromatics analytes of 1 ng/mL with an I50 of 5 ng/mL was observed. No cross reactivity with mononitroaromatic compounds was observed. Antibodies developed to mononitroaromatic haptens showed high affinity for a variety of coating antigens but would not compete with nitroaromatic analytes in a normal ELISA. 

Phenol B.P. M.P. Bromo Com- pound Acetate Benzoate p-NItro- benzoate 3 S Dl-nitro-benzoate Aryloxy- acetic Acid NN-Ol- phenyl- carba- mate N-a- naphthyl- carba- mate p-Tolu- enesul- phonate 2 4- Dinitro- phenyl Ether... 

The nitration of nitro- and dinitro-biphenyls has been examined by several workers. i - As would be expected, nitration of the nitro-biphenyls occurs in the phenyl ring. Like a phenyl group, a nitrophenyl group is 0 -directing, but like certain substituents of the type CH CHA ( 9.1.6) it is, except in the case of w-nitrophenyl, deactivating. Partial rate factors for the nitration at o °C of biphenyl and the nitro-biphenyls with solutions prepared from nitric acid and acetic anhydride are given below. The high o p-v2X o found for nitration of biphenyl... 

N-(4-nitrophenyl)-amino acids N-(2,4-dinitrophenyl)-amino acids 8) and 3-nitro-2-pyridyl amino acids have been of considerable interest. A generally applicable mechanistic scheme does not exist so far, and except for 3-nitrophenyl acetate in ortho and/or -para position of the phenyl (pyridyl) ring seems to be a prerequisite for efficient decarboxylation. 

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