Patent EP-2546229-A1 (EP)
Inventor: HEINRICH MARKUS
IPC: C07C213/08
Filed: 2011-07-15
Abstract: Synthesis of 2-aminobiphenylene compound (III) comprises reacting a benzene diazonium salt (I) with an aniline compound (II) under basic reaction conditions. Synthesis of 2-aminobiphenylene compound of formula (III) comprises reacting a benzene diazonium salt of formula (I) with an aniline compound of formula (II) under basic reaction conditions. R 1> : halo, alkyl, haloalkyl, hydroxy, hydroxyalkyl, alkoxy, haloalkoxy, alkylthio, cycloalkyl, haloalkylthio, alkenyl, alkynyl, amino, nitro, cyano, -SO 3R 5>, -SO 2NH 2, -SO 2NHR 4>, -SO 2NR 4>R 5>, -COOR 4>, -CONHR 4>, -CONR 4>R 5>, -COR 4>, -OCOR 4>, -NR 4>R 5>, -NR 4>COR 5>, -NR 4>SO 2R 5>, alkylcarbonyl, haloalkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkenyloxycarbonyl, alkylsulfonyl, haloalkylsulfonyl, alkylimino, aryl, aryloxy, arylcarbonyl, arylalkyl, heteroarylalkyl, arylalkoxycarbonyl, arylalkylimino or heteroaryl; X -> : halide, hydrogen sulfate, sulfate, tetrafluoroborate, acetate, trifluoroacetate, hexafluorophosphate, hexafluoroantimonate, anion of aryl 1,2-dicarboximide or anion of aryl 1,2- disulfonic acid imide; either R 2>, R 3> : H, alkyl, hydroxyalkyl, aminoalkyl, cycloalkyl, haloalkyl, -(CH 2) n-OR 4>, -(CH 2) n-NR 4>R 5>, -(CH 2) n-NR 4>COR 5>, -(CH 2) n-NR 4>COOR 5>, -(CH 2) n-COOR 4>, -(CH 2) nCONHR 4>, -(CH 2) n-CONR 4>R 5>, -(CH 2) n-SO 3R 4>, -(CH 2) n-CN, arylalkyl, heteroarylalkyl, aryl or heteroaryl; and R 10> : H, halo, alkyl, haloalkyl, hydroxyalkyl, cycloalkyl, arylalkyl, heteroarylalkyl, -(CH 2) q-NR 4>R 5>, -(CH 2) q-NR 4>COR 5>, -(CH 2) q-NR 4>COOR 5>, -(CH 2) q-COOR 4>, -(CH 2) q-CONHR 4>, -(CH 2) q-CONR 4>R 5>, -(CH 2) q-SO 3R 4>, -(CH 2) q-CN, aryl or heteroaryl; or R 2>R 3> : alkylidene group; or R 2>R 3>N, R 2>R 10>, R 3>R 10> : a non-aryl 4-7-membered ring optionally containing 1-3 further heteroatoms of O, S or N; n : 1-10; R 4>, R 5> : H, alkyl, cycloalkyl, haloalkyl, arylalkyl, heteroarylalkyl, aryl or heteroaryl; R 6> : H, halo, alkyl, alkenyl, alkynyl, cycloalkyl, arylalkyl, heteroarylalkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, aryloxyalkyl, heteroaryloxyalkyl or aminoalkyl, -(CH 2) n-NR 4>R 5>, -COOH, -CHO, -CN, -COR 4>, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, arylalkylcarbonyl, alkenylcarbonyl, arylcarbonyl, heteroarylcarbonyl, -COOR 4>, alkoxycarbonyl, haloalkoxycarbonyl, cycloalkoxycarbonyl, arylalkoxycarbonyl, alkenyloxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, -CONHR 4>, -CONR 4>R 5>, amino, nitro, -NHR 4>, -NR 4>R 5>, 1-pyrrolidino, 1-piperidino, 1-morpholino, alkylimino, cycloalkylimino, haloalkylimino, arylalkylimino, -NR 4>COR 5>, -NR 4>COOR 5>, -NR 4>SO 2R 5>, hydroxy, alkoxy, haloalkoxy, cycloalkoxy, arylalkyloxy, aryloxy, heteroaryloxy, -OCOR 4>, alkylcarbonyloxy, haloalkylcarbonyloxy, cycloalkylcarbonyloxy, arylalkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy, -OCONR 4>R 5>, -O-(CH 2) n-OR 4>, -O-(CH 2) n-NR 4>R 5>, -O-(CH 2) n-NR 4>COR 5>, -O-(CH 2) n-NR 4>COOR 5>, -O-(CH 2) n-COOR 4>, -O-(CH 2) n-CONHR 4>, -O-(CH 2) n-CONR 4>R 5>, -O-(CH 2) n-SO 3R 4>, -O-(CH 2) n-SO 2R 4>, -O-(CH 2) n-CN, -SH, alkylthio, haloalkylthio, cycloalkylthio, arylalkylthio, arylthio, heteroarylthio, alkylsulfonyl, haloalkylsulfonyl, cycloalkylsulfonyl, arylalkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, -SO 2NH 2, -SO 2NHR 4>, -SO 2NR 4>R 5>, -SO 3R 5>, aryl or heteroaryl; q : 1-5; and m : 0-5. An independent claim is included for the preparation of a diphenyl compound of formula (X) comprising preparing (III) by the above process. Z : aryl or 5- or 6-membered heteroaryl having 1-4, preferably 1-3 heteroatoms of N (preferred), O or S (both optionally substituted by 1-4 halo, 1-4C-alkyl, 1-4C-haloalkyl (all preferred), 1-4C-alkoxy or 1-4C-haloalkoxy). [Image] [Image] ACTIVITY : Pesticide. MECHANISM OF ACTION : None given.