Patent ID: 6242605
Filing Date: 2001-06-05
Classification: C07C,C07D

Abstract:
A process for the production of a compound of the formula: ##STR53##wherein:R.sup.1 and R.sup.2 are, independently, selected from H; C.sub.1 -C.sub.12 alkyl or C.sub.1 -C.sub.6 perfluorinated alkyl;X selected from halogen, --O--SO.sub.2 --CH.sub.3, --O--SO.sub.2 --CF.sub.3, or a moiety of the structure: ##STR54##Z is --NO.sub.2, halogen, --CH.sub.3 or --CF.sub.3 ;m is an integer from 0 to 3;R.sup.3, R.sup.4, R.sup.5, and R.sup.6 are independently selected from H, halogen, --NO.sub.2, alkyl, alkoxy, C.sub.1 -C.sub.6 perfluorinated alkyl, OH or the C.sub.1 -C.sub.4 esters or alkyl ethers thereof, --CN, --O--R.sup.1, --O--Ar, --S--R.sup.1, --S--Ar, --SO--R.sup.1, --SO--Ar, --SO.sub.2 --R.sup.1, --SO.sub.2 --Ar, --CO--R.sup.1, --CO--Ar, --CO.sub.2 --R.sup.1, or --CO.sub.2 --Ar; andY is a six-membered saturated, unsaturated or partially unsaturated heterocycle containing up to two heteroatoms selected from the group consisting of --O--, --NH--, --N(C.sub.1 C.sub.4 alkyl)--, --N.dbd., and --S(O).sub.n --, wherein n is an integer of from 0-2, substituted or unsubstituted with 1-3 substituents independently selected from the group consisting of hydrogen, hydroxyl, halo, C.sub.1 -C.sub.4 alkyl, trihalomethyl, C.sub.1 -C.sub.4 alkoxy, trihalomethoxy, C.sub.1 -C.sub.4 acyloxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, hydroxy (C.sub.1 -C.sub.4)alkyl, phenyl substituted or unsubstituted with 1-3 (C.sub.1 -C.sub.4)alkyl, --CO.sub.2 H, --CN, --CONHR.sup.1, --NH.sub.2, C.sub.1 -C.sub.4 alkylamino, C.sub.1 -C.sub.4 dialkylamino, --NHSO.sub.2 R.sup.1, --NHCOR.sup.1, or --NO.sub.2 ;the process comprising the steps of:a) alkylating a hydroxybenzaldehyde of the formula: ##STR55##wherein R.sup.3 -R.sup.6 are as defined above, with an alkyl halide of the formula: ##STR56##wherein R.sup.1, R.sup.2 and Y are as defined above, m is an integer from 0 to 3 and halo is Cl, F, Br or I, to produce an aldehyde of the formula: ##STR57##b) reducing the aldehyde product of step a), to yield an alcohol of the formula: ##STR58##c) converting the alcohol of step b) to its hydrochloride salt; andd) converting the alcohol group in the compound of step c) to a leaving group.