N-substituted ortho-aminoarylketimines

摘要

Compounds having, in one tautometic form, the general formula (in which R1 is a hydrogen or halogen atom, a trifluoromethyl group, a C1- 7 alkyl or alkoxy group or a nitro or amino group, R2 is a phenyl group which may be substituted by a halogen atom, by a trifluoromethyl or nitro group or by a C1- 7 alkyl or alkoxy group, or is a C1- 7 alkyl, C5- 7 cycloalkyl, furyl or thienyl group, R3 is hydrogen atom or C1- 7 alkyl group, R4 is a hydrogen atom, a C1- 7 alkyl group, a C2- 7/t alkylthioalkyl group, a C2- 8 carbalkoxy group, a carbamoyl group, an alkylcarbamoyl, dialkylcarbamoyl or dialkylaminoalkylcarbamoyl group having 1-7 carbon atoms in the or each alkyl group, or a group -COOCat in which Cat is the cation of an alkali metal or semication of an alkaline earth metal and R5 is a C1- 7 alkyl group or, when R4 is a carbamoyl or -COOCat group, a cation Cat) are prepared by (a) -excluding the case in which R4 is -COOCat and/or R5 is Cat-reacting a ketimine of the formula with an ester of the formula H2NCHR4COOR5 or a salt thereof, (b)-in the case of alkali metal salts of the formula saponifying a corresponding diester with an alkali metal hydroxide or treating a benzodiazepine derivative of the formula (in which Alk is a C1- 7 alkyl group) with an alkali metal hydroxide in a C1- 7 alkanol, (c)-in the case of alkali metal salts of the formula treating a benzodiazepine derivative of the formula with an alkali metal hydroxide in a C1- 7 alkanol, or (d)-in the case of alkaline earth metal salts-treating a corresponding alkali metal salt with an appropriate alkaline earth metal salt. In some cases the chelate and non-chelate forms may be separated by fractional crystallization.