IE34016B1 - New omikron-anilino-phenylethyl alcohols, the production thereof and compositions containing same - Google Patents

Abstract

1304622 Ortho-anilino-phenethyl alcohols CIBA-GEIGY AG 19 Feb 1970 [20 Feb 1969] 7912/70 Heading C2C Novel compounds of the Formula I wherein R 1 , R 2 and R 3 are independently hydrogen, chlorine, fluorine, bromine, methyl or ethyl and R 1 may additionally be trifluoromethyl and R 4 is hydrogen, chlorine, fluorine, bromine, methyl or methoxy may be prepared by reducing the corresponding o-anilino-phenyl acetic acid or an ester thereof or hydrolysing the corresponding N-acylated compound. The corresponding o-anilino-phenyl acetric acid may be formed by reductive ring opening of an N-phenyl substituted indole-2,3-dione or hydrolytic ring opening of an N-phenylsubstituted-2-indolinone, in which, when present, a substituent corresponding to the R 4 position in I is converted from hydroxy to methoxy. N - Phenyl - 2,61 - dichloroaceto - o - toluidide may be prepared by acetylation of 6-chloro-otoluidine to yield 6<SP>1</SP> - chloroaceto - o - toluidine followed by treatment with bromobenzene in the presence of copper and base to yield 6-chloro-N- phenyl-aceto-o-toluidide which is reacted with chloroacetyl chloride to yield the required compound. Similarly 2 - chloro - N - (2,6 - dichlorophenyl).aceto-p-anisidide may be prepared by reaction of 2<SP>1</SP>,6<SP>1</SP>-dichloroacetanilide with pbromoanisole in the presence of copper and base to yield .N-(2,6-dichlorophenyl)-p-anisidine which is reacted with chloroacetyl chloride to yield the required compound. The intermediate indole-2,3-dione 1-(2,6- xylyl) - indole - 2,3 - dione may be prepared by reaction of o-chlorobenzoic acid with 2,6- xylidine in the presence of base to yield N- (2,6-xylyl)-anthranilic acid which is decarboxylate to yield N-phenyl-2,6-xylidine which with oxalyl chloride yields N.phenyl-2<SP>1</SP>, 6<SP>1</SP>-dimethyl'- oxaniloyl chloride which may be cyclized in the presence of aluminium chloride to the required compound. Pharmaceutical compositions of compounds I show antiphlogistic, analgesic and antipyretic activity when administered orally, parenterally, rectally or topically with the usual excipients. [GB1304622A]