Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1975-04-04
1976-03-02
Trousof, Natalie
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
260240G, 2603409, 260566AE, 260566R, 260578, 260999, C07D23360
Patent
active
039418022
ABSTRACT:
Compounds of the formulae IV and V: ##SPC1##
wherein R.sub.o and R.sub.1 are hydrogen or alkyl of 1 to 3 carbon atoms, inclusive; wherein R.sub.2 is hydrogen, fluoro, chloro, or trifluoromethyl; wherein R.sub.3 is hydrogen or fluoro with the proviso that R.sub.3 cannot be fluoro, if R.sub.2 is chloro or trifluoromethyl; and wherein R.sub.4 is hydrogen, fluoro, chloro, bromo, trifluoromethyl, or nitro, are obtained by a multi-step reaction from the corresponding .alpha.-(phenyl)-o-toluidine of the formula I ##SPC2##
wherein R.sub.2, R.sub.3, and R.sub.4 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.
REFERENCES:
patent: 3526636 (1970-09-01), Houlihan
patent: 3534061 (1970-10-01), Black
patent: 3763178 (1973-10-01), Sulkowski
patent: 3763179 (1973-10-01), Gall
Berneis Hans L.
The Upjohn Company
Trousof Natalie
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