4- Chloro phenylacetic acid

Biological. Reported degradation products by the microorganism Alcaligenes BM-2 for a mixture of polychlorinated biphenyls include monohydroxychlorobiphenyl, 2-hydroxy-6-oxo-chlorophenylhexa-2,4-dieonic acid, chlorobenzoic acid, chlorobenzoylpropionic acid, chloro-phenylacetic acid, and 3-chlorophenyl-2-chloropropenic acid (Yagi and Sudo, 1980). 

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... 

The reaction has also been applied to the conversion of vinyl bromides into acrylic acids, e.g. 1-bromo- and 1-chlorocyclooctene are converted into cyclooctene-1-carboxylic acid (ca. 98%) [3], 2-chloro-3,3-dimethylbut-l-ene yields 4,4-dimethylpent-2-enoic acid (95%), and tams-cinnamic acid is obtained (85%) from fran.v-p-bromostyrene. cis-p-Bromostyrene produces a mixture of cis- and trans-cinnamic acids in 38 and 42% yields, respectively [3]. In these reactions, benzyltri-ethylammonium chloride cannot be used as the phase-transfer catalyst, as it leads to the production of phenylacetic acid [3]. 

Disposition in the Body. Variably absorbed after oral or rectal administration and distributed into the synovial fluid. Metabolised by glucuronic acid conjugation, some conjugation with glycine, deallylation to form 3-chloro-4-hydroxyphenylacetic acid, and hydroxylation to form 3-chloro-4-(2,3-dihydroxypro-pyloxy)phenylacetic acid, which may be methylated an epoxide... 

Pyridine-N-oxide [1, 966]. a-Bromo and a-chloro carboxylic acids are oxidatively decarboxylated by treatment with pyridine-N-oxide (4 equiv.) in refluxing benzene or toluene.3 Cohen et at. note that, since pivalic acid is completely inert to pyridine-N-oxide, an u-hydrogen atom appears to be essential, for example in the reaction of phenylacetic acid. They suggest that an a-pyridinium ion is an intermediate ... 

Organo-tin and -silicon steroids have been prepared from 3a- and 3)S-halocho-lest-anes and 5-enes, and a number of steroidal esters of p-[AfAT-bis(2-chloro-ethyl)amino]phenylacetic acid and sulphides derived from p-bis(2-chloroethyl)-amino-thiophenol and ethylenimine derivatives of steroids have been prepared. The substituted phenylacetates showed good inhibition of certain tumours. ... 

Pbeaesterlne. Cholest-5-en-3p-oi 4-[bis< 2-chloro-ethyl)aminojbenzeneacetare p-[bis(2-chtoroethyi)amino]-phenylacetic acid cholesterol ester cholesteryl p-bis(2-ch]oro-ethyljaminophenylaeetate Fenesterin Fenestrin. CwH C j-NOumol wt 644.82. C 72.65%, H 9.22%, Cl 11.00%, N... 

Chloro-2-phenylacetic acid 945 Ethyl mandelate (0.75 mole from mandelic acid and ethanol-HCl) is dissolved in SOCl2 (0.82 mole), and the solution is set aside at room temperature for 16 h, heated on a water-bath for 30 min, and poured into ice-water. The ethyl 2-chloro-2-phenylacetate formed (81-85 % yield) is extracted with ether and, after isolation, is hydrolysed by a boiling mixture of glacial acetic acid and concentrated hydrochloric acid. 

The interaction between the sodium salt of phenylacetic acid and isopropyl magnesium bromide results into a doubly charged species known as the Ivanov reagent. This product on treatment with cyclopentanone affords aldol condensation to yield the corresponding hydroxy acid. The resulting product on being subjected to alkylation with N-(2-chloro-ethyl)-dimethylamine gives the desired official compound. 

A one-pot two-step synthesis of hydroxystilbenes with trans selectivity was developed through a modified Perkin reaction between benzaldehydes and phenylacetic acids bearing 4- or 2-hydroxy substitution at the aromatic ring [67]. The reaction was performed under mild conditions in the presence of piperidine-methylimidazole and polyethylene glycol under microwave irradiation. As a result, 71% yield of ( )-4-chloro-4 -hydroxy-3 -methoxystilbene from 4-hydroxy-3-methoxybenzaldehyde and 4-chlorophenylacetic acid was obtained. A microwave-induced one-pot process for the preparation of arylethenes has been patented [118]. For the preparation of a series of arylethenes (I R -R = H, OH, OMe, AcO, halo, NO2 R, R, R = OH, AcO R= H, substituted aryl), reaction of 2- or 4-hydroxy substituted cinnamic adds or derivatives in the presence of a base, under reflux or microwave irradiation, has been used. For example, a mixture of a-phenyl-4-hydroxy-3-methoxycinnamic acid, NaHC03, methylimidazole, and polyethylene glycol was microwaved at 200 W and 180 °C for 10 min to give 96% 4-hydroxy-3-methoxystilbene. 

A number cf -substituted phenylacetic and 2-phenylbutyric aqids have been prepared and tested by Canonica et al. [216]. The substituted phenylacetic acids were found to be devoid of hypocholesterolemic activity. In the a-phenylbutyric acid series the am-substituted hydroxyl and amino derivatives showed a decreased activity, while the am-substituted methyl, methoxy and chloro derivatives led to an increase of activity over the parent compound XLVIII. The aminoethanol salt of 2-phenylbut5nic acid caused a significant reduction in plasma cholesterol levels in patients. In subjects with normal plasma cholesterol concentration the drug was reported to be without effect [217, 218]. Cholesterol-lowering and antineuralgic properties have been claimed for the anihde LXIX of 2-phenylbut5nric acid [219]. 

A -Aiyloxindoles 192, which are intermediates for the preparation of pharmacologically active 2-(iV-arylamino)-phenylacetic acids 193 were obtained by the Smiles rearrangement of substituted iV-chloroacetyl-diarylamines 191. The rearrangement of 2-chloro-6-fluoro- and 2,6-difluoro-phenoxy- derivatives proceeded affording the expected product along with a major side reaction, which has been minimized by utilization of proper choice of reaction conditions. 

A mixture of phenylacetic acid, benzyl alcohol, and tri-n-butylamine in methylene chloride added under argon to a mixture of l-methyl-2-bromopyridinium iodide and methylene chloride, and refluxed 3 hrs. benzyl phenylacetate. Y 97%. F. e., also with l-methyl-2-chloropyridinium iodide, s. T. Mukaiyama et al., Chem. Lett. 1975, 1045 Bull. Chem. Soc. Japan 50, 1863 (1977) carboxylic acid amides from amines (cf. Synth. Meth. 26, 367) s. ibid. 1975, 1163 3,4-dihydro-2H-pyrido-[1,2-a]pyrimid-2-one as acid scavenger cf. ibid. 1976, 13, 57 lactones from hydroxycarboxylic acids (cf. Synth. Meth. 17, 320) with 2-chloropyridine methio-dide and triethylamine s. ibid. 1976, 49 esters with 2 halogeno-3-ethylbenzothia-zolium salts of ibid. 1976, 267 2-chloro-N-methylbenzothiazolium triflate as condensing agent s. F. Souto-Bachiller, G. S. Bates, and S. Masamune, Chem. Com-mun. 1976, 719. 

Obtained by Friedel-Crafts acylation of p-chloro-phenol with phenylacetic acid in the presence of boron trifluoride at 160° for 4 h in a sealed tube (68%) [5187]. 

Dhavale, D. D., Mali, V. R, Sudrik, S. G., and Sonawane, H. R., Media controlled photo-Favorskii type rearrangement of a-chloro acetophenones synthesis of phenylacetic acids. Tetrahedron, 53,... 

A related agent, g1icetanile sodiurn (42), is made by a variant of this process. Methyl phenylacetate is reacted with chlorosulfonic acid to give which itself readily reacts with ami nopyrimidine derivative 39 to give sulfonamide Saponification to acid is followed by conversion to the acid chloride and amide formation with 5-chloro-2-methoxyaniline to complete the synthesis of the hypoglycemic agent glicetanile (42). ... 

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