Method for synthesising aminobiphenyls

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This patent discloses a method for synthesizing 2-aminobiphenyl compounds and their derivatives by reacting a benzene diazonium salt with an aniline compound under basic conditions. The process uses accessible starting materials and avoids expensive or toxic transition metals typically used in biaryl formation. The resulting aminobiphenyls are useful intermediates in making bioactive molecules, especially pharmaceuticals and agrochemicals.

Use CasesContent extracted from patent full text and abstract with AI.

• Production of intermediates for pharmaceutical drug synthesis, such as γ-secretase inhibitors for Alzheimer's disease.
• Manufacture of active ingredients or intermediates for agrochemicals and pesticides.
• Preparation of functional materials where aminobiphenyl moieties impart special properties (e.g., in dyes or polymers).
• Academic or industrial synthesis of complex biphenyl structures for research or new product development.

BenefitsContent extracted from patent full text and abstract with AI.

• Cost-effective and scalable process using inexpensive and readily available starting materials (anilines and diazonium salts).
• Environmentally friendlier than traditional metal-catalyzed coupling techniques by avoiding toxic or precious metals.
• The broad substrate scope enables synthesis of structurally diverse aminobiphenyls, expanding chemical space for drug discovery and agrochemical R&D.
• High selectivity and good yields, with the potential for reduced side products and easier purification.
• Amenable to various reaction conditions—including electrochemical or photochemical versions—for further optimization or green chemistry initiatives.

Technical Classifications (CPCs)

Inventors & Applicants

Patent 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.