Indoline derivatives

Details Indoline derivatives Indoline derivatives

C - Chemistry, Metallurgy

07

D

260/207.7

C07D 209/26 (2006.01)

Patent

CA 1056821

ABSTRACT OF THE DISCLOSURE This invention relates to a process for the preparation of a compound of the following formula: Image A wherein R1 is selected from the group consisting of hydrogen, chloro, bromo, lower alkoxy, nitro, amino, acetamido and dimethylamino; R2 is selected from the group consisting of hydrogen, lower alkoxy and nitro, or R1 and R2 together form a methylenedioxy group; R3 is selected from the group consist- ing of hydrogen and methyl; Y is selected from the group consisting of hydroxy, chloro, bromo, methanesulfonyloxy and p-toluenesulfonyloxy, which comprises either;- (a) lower alkanoylating or bensoylating a compound of the formula Image where R1 , R2, R3 and Z are as defined above; or (b) reducing an acid of the formula: Image or a lower ethyl ester or anhydride thereof, wherein R1, R2, R3 and Y are as defined above, to produce a compound of formula I in which Z is hydroxy; or (c) partially hydrolyzing a compound of the formula: Image in which "Acyl" represents an acyl group and R1, R2, R3 and Y are as previously defined; when a compound of formula I is required in which R1 is chloro, bromo or nitro, chlorinating, brominating or nitrating a corresponding compound of formula I in which R1 is a hydrogen atom; when a compound of formula I is required in which R2 is nitro nitrating a corresponding com- pound of formula I in which R2 is a hydrogen atom; when a compound of for- mula I is required in which R1 is amino reducing a corresponding compound of formula I in which R1 is nitro; and when a compound of formula I is required in which Z is chloro, bromo, methanesulfonyloxy or p-toluenesulfo- nylating a corresponding compound formula I in which Z is hydroxy. The compounds of formula A are useful as intermediates in the preparation of corresponding substituted 3-[2-(4-phenyl-1-piperazinyl)ethyl]indolines useful as tranquilizing agents.

276961

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