C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/315.25
C07D 233/56 (2006.01) C07D 317/28 (2006.01) C07D 521/00 (2006.01)
Patent
CA 1060027
ABSTRACT OF THE DISCLOSURE Compounds of the formulae IV and V: Image IV Image V wherein R0 and R1 are hydrogen or alkyl of 1 to 3 carbon atoms, inclusive; wherein R2 is hydrogen, fluoro, chloro, or trifluoromethyl; wherein R3 is hydrogen or fluoro with the proviso that R3 cannot be fluoro, if R2 is chloro or trifluoromethyl; and wherein R4 is hydrogen, fluoro, chloro, bromo, trifluoromethyl, or nitro, are obtained by -1- a multi-step reaction from the corresponding .alpha.-(phenyl) o-toluidine of the formula I: Image wherein R2, R3, and R4 are defined as above, by treating I in sequence with an alkyl ester of orthoformic acid the resulting product with 2-alkyl-2-(aminoalkyl)-1,3- dioxolane or a 2-amino-alkanone dialkyl ketal and finally with titanium tetrachloride to obtain compound IV, and oxidizing compound IV to obtain the corresponding compound V. Compounds IV and V have minor tranquilizing activity which can be utilized to calm mammals or birds. Their more important use, however, is as intermediates in the production of the strongly sedating and tranquilizing imidazolobenzodiazepines. -1a-
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