Patent EP-0063826-A2 (EP)
Inventor: GRISS GERHART DR DIPL-CHEM
IPC: C07D295/20
Filed: 1980-06-28
Abstract: 1. Claims for the Contracting States : BE, CH, DE, FR, GB, IT, LI, LU, NL, SE 2-Amino-benzoic acid derivatives of general formula I  see diagramm : EP0063826,P14,F2  wherein R1 represents a fluorine, chlorine or bromine atom, an amino, cyano or hydroxy group, an alkoxy group with 1 to 3 carbon atoms optionally substituted by a phenyl group, or an alkoxy group with 4 to 6 carbon atoms, R2 and R3 together with the nitrogen atom between them represent an N-alkylcyclohexylamino group wherein the alkyl moiety may contain 2 to 4 carbon atoms, an N-alkyl-phenylamino or N-alkyl-benzylamino group wherein the alkyl moiety may contain 1 to 3 carbon atoms, a cyclic alkyleneimino group with 6 to 12 carbon atoms, a piperidino group substituted by an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 3 carbon atoms, an alkoxycarbonyl group with a total of 2 to 4 carbon atoms or a phenyl group, or a piperidino group substituted by 2, 3 or 4 alkyl groups each having 1 to 3 carbon atoms, a morpholino or thiomorpholino group optionally substituted by one or two alkyl groups each having 1 to 3 carbon atoms, a piperazino group substituted in the 4 position by an alkyl group with 1 to 3 carbon atoms, an alkoxycarbonyl group with a total of 2 to 4 carbon atoms, a phenyl, halophenyl, pyridyl, benzyl or furoyl group, a saturated or partially unsaturated azabicycloalkyl group with 8 to 10 carbon atoms, a 1,4-dioxa-8-aza-spiro-alkane group with a total of 6 to 8 carbon atoms, a pyrrolidino or tetrahydro-pyridino group and W represents a carboxyl, aminocarboxyl, cyano or carbalkoxy group with a total of 2 to 4 carbon atoms, and the acid addition salts thereof with inorganic or organic acids or bases if W represents the carboxyl group. 1. Claims for the Contracting State : AT Process for preparing 2-amino-benzoic acid derivatives of general formula I  see diagramm : EP0063826,P15,F4  wherein R1 represents a fluorine, chlorine or bromine atom, an amino, cyano or hydroxy group, an alkoxy group with 1 to 3 carbon atoms optionally substituted by a phenyl group, or an alkoxy group with 4 to 6 carbon atoms, R2 and R3 together with the nitrogen atom between them represent an N-alkylcyclohexylamino group wherein the alkyl moiety may contain 2 to 4 carbon atoms, an N-alkyl-phenylamino or N-alkyl-benzylamino group wherein the alkyl moiety may contain 1 to 3 carbon atoms, a cyclic alkyleneimino group with 6 to 12 carbon atoms, a piperidino group substituted by an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 3 carbon atoms, an alkoxycarbonyl group with a total of 2 to 4 carbon atoms or a phenyl group, or a piperidino group substituted by 2, 3 or 4 alkyl groups each having 1 to 3 carbon atoms, a morpholino or thiomorpholino group optionally substituted by one or two alkyl groups each having 1 to 3 carbon atoms, a piperazino group substituted in the 4 position by an alkyl group with 1 to 3 carbon atoms, an alkoxycarbonyl group with a total of 2 to 4 carbon atoms, a phenyl, halophenyl, pyridyl, benzyl or furoyl group, a saturated or partially unsaturated azabicycloalkyl group with 8 to 10 carbon atoms, a 1,4-dioxa-8-aza-spiro-alkane group with a total of 6 to 8 carbon atoms, a pyrrolidino or tetrahydro-pyridino group and W represents a carboxyl, aminocarboxyl, cyano or carbalkoxy group with a total of 2 to 4 carbon atoms, and the acid addition salts thereof with inorganic or organic acids or bases if W represents the carboxyl group, a) in order to prepare compounds of general formula I wherein R1 is an amino group, a nitro compound of general formula II  see diagramm : EP0063826,P16,F2  wherein R2 , R3 and W are as hereinbefore defined, is reduced, or b) in order to prepare compounds of general formula I wherein R1 is a hydroxy group, a cyano group or a fluorine, chlorine or bromine atom, a compound of general formula Ia  see diagramm : EP0063826,P16,F4  wherein R2 , R3 and W are as hereinbefore defined, is converted with a nitrite into a diazonium salt and the diazonium salt thus obtained is subsequently converted into the corresponding compound by heating in the presence of sulphuric acid, copper or a corresponding copper(I)salt, or c) in order to prepare compounds of general formula I wherein R1 represents an alkoxy group with 1 to 3 carbon atoms optionally substituted by a phenyl group or an alkoxy group with 4 to 6 carbon atoms, a hydroxy compound of general formula Ib  see diagramm : EP0063826,P16,F1 wherein R2 , R3 and W are as hereinbefore defined, is alkylated with a compound of general formula III Z-R'1 wherein R'1 represents an alkyl group with 1 to 3 carbon atoms optionally substituted by a phenyl group or an alkyl group with 4 to 6 carbon atoms and Z represents a nucleophilic leaving group or together with the adjacent hydrogen atom of the group R'1 represents a diazo group, and subsequently, if desired, hydrolysis is carried out and subsequently, if desired, a compound of general formula I thus obtained wherein W represents a cyano, aminocarbonyl or alkoxycarbonyl group is converted by hydrolysis into a corresponding compound of general formula I wherein W represents a carboxyl group and/or a compound of general formula I thus obtained is converted into the acid addition salts thereof with inorganic or organic acids or bases if W represents a carboxyl group.