Patent ID: 8598222

Claim:
A process for preparing 1,3,4-substituted pyrazole compounds of the formula I in which X is a CX 1 X 2 X 3 group in which X 1 , X 2 and X 3 are each independently hydrogen, fluorine or chlorine, where X 1 may also be C 1 -C 6 -alkyl or C 1 -C 4 -haloalkyl and where at least one of the X 1 , X 2 radicals is different from hydrogen, R 1 is C 1 -C 4 -alkyl or cyclopropyl, and R 2 is CN or a CO 2 R 2a group in which R 2a is C 5 -C 6 -cycloalkyl, optionally substituted phenyl or C 1 -C 6 -alkyl which may optionally be substituted by C 1 -C 4 -alkoxy, phenyl or C 3 -C 6 -cycloalkyl, comprising i) reacting a compound of the formula II with a hydrazone of the formula III wherein Y is oxygen, an NR y1 group or an [NR y2 R y3 ] + Z − group, in which R y1 , R y2 and R y3 are each independently C 1 -C 6 -alkyl, C 5 -C 6 -cycloalkyl, optionally substituted phenyl or optionally substituted phenyl-C 1 -C 4 -alkyl, or R y2 and R y3 together with the nitrogen atom to which they are bonded are an N-bonded, 5- to 8-membered, saturated, optionally substituted heterocycle which, as well as the nitrogen atom, may also comprise 1 or 2 further heteroatoms selected from N, O and S as ring atoms, and Z − is an anion; R 3 is OR 3a or an NR 3b R 3c group, in which R 3a , R 3b and R 3c are each independently C 1 -C 6 -alkyl, C 5 -C 6 -cycloalkyl, optionally substituted phenyl or optionally substituted phenyl-C 1 -C 4 -alkyl, or R 3b and R 3c together with the nitrogen atom to which they are bonded are an N-bonded 5- to 8-membered, saturated, optionally substituted heterocycle which, as well as the nitrogen atom, may also comprise 1 or 2 further heteroatoms selected from N, O and S as ring atoms, and R 4 and R 5 are each independently hydrogen, C 1 -C 6 -alkyl which may optionally be substituted by C 1 -C 4 -alkoxy, phenyl or C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl or optionally substituted phenyl, where at least one of the R 4 and R 5 radicals is different from hydrogen, or R 4 and R 5 together with the carbon atom to which they are bonded may also be a 5- to 10-membered saturated carbocycle which is optionally mono- or polysubstituted by C 1 -C 4 -alkyl groups and/or optionally substituted phenyl, and/or comprises one or 2 fused phenyl rings; ii) treating the reaction product obtained with an acid in the presence of water.