Preparing beta-aryloxime compounds, useful as intermediates in the chemical and pharmaceutical industries, comprises reacting aryl diazonium compounds with (hetero)alkyl(aryl)ene compounds in the presence of nitric oxide

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This patent describes a method for synthesizing beta-aryloxime compounds by reacting aryl diazonium compounds with (hetero)alkyl(aryl)ene compounds in the presence of nitric oxide. The resulting compounds serve as important intermediates in the production of chemicals and pharmaceuticals.

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

• Production of beta-aryloxime compounds for use as intermediates in pharmaceutical synthesis
• Manufacturing of fine chemicals and specialty chemicals
• Development of agrochemicals and dyes using beta-aryloxime intermediates
• Research in synthetic organic chemistry involving new oxime derivatives

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• Provides a new synthetic pathway for beta-aryloxime compounds, potentially improving efficiency and yield
• Broad applicability due to the flexible substituent groups on reactants
• Enables access to a variety of functionalized beta-aryloximes, useful for multiple industries
• May reduce reliance on more hazardous or less efficient synthetic methods

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Inventors & Applicants

Patent Abstract

Preparing beta-aryloxime compounds (I) comprises reacting aryl diazonium compounds (II) with (hetero)alkyl(aryl)ene compounds (III) in the presence of nitric oxide. Preparing beta-aryloxime compounds of formula (I) comprises reacting aryl diazonium compounds of formula (II) with (hetero)alkyl(aryl)ene compounds of formula (R3-CH=CH-R2) (III) in the presence of nitric oxide. R1 : H, halo, (cyclo)alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, aminoalkyl, -COOR7, -CONH 2, -CONHR7, -CONR7R8, -COR7, cyano, amino, -NHR7, -NR7R8, -NR7COR8, -NR7SO 2R8, nitro, hydroxy, (halo)alkoxy, -OCOR7, (halo)alkylthio, -SO 3R8, -SO 2NH 2, -SO 2NHR7, -SO 2NR7R8, (halo)alkylsulfonyl, alkylimino, (hetero)aryl (optionally substituted by 1-5 groups comprising halo, (halo)alkyl or (halo)alkoxy), aryloxy, arylcarbonyl, arylalkyl, arylmethoxycarbonyl or arylalkylimino; either R2 : H, -COOR7, -CONH 2, -CONHR8, -CONR7R8, -COR7, -CN, -NHR7, -NR7R8, -NR7COR8, -NR7SO 2R8, nitro, (halo)alkoxy, -OCOR7, -SO 3R8, -SO 2NH 2, -SO 2NHR7, -SO 2NR7R8, (halo)alkylsulfonyl, (hetero)aryl (optionally substituted by 1-5 groups comprising halo, (halo)alkyl, hydroxy, (halo)alkoxy, -COOR7, -CONH 2, -CONHR8, -CONR7R8, -COR7, -CN, -NHR7, -NR7R8, -NR7COR8, -NR7SO 2R8, nitro, -OCOR7, -SO 3R8, -SO 2NH 2, -SO 2NHR7, -SO 2NR7R8 or (halo)alkylsulfonyl), aryloxy, arylcarbonyl or arylmethoxycarbonyl; and R3 : H, (cyclo)alkyl, haloalkyl, arylalkyl, hydroxyalkyl, aminoalkyl, alkoxyalkyl, -COOR7, -CONH 2, -CONHR8, -CONR7R8, -COR7, -CN, -NHR7, -NR7R8, -NR7COR8, -NR7SO 2R8, nitro, (halo)alkoxy, -OCOR7, -SO 3R8, -SO 2NH 2, -SO 2NHR7, -SO 2NR7R8, (halo)alkylsulfonyl, (hetero)aryl (optionally substituted by 1-5 groups comprising halo, (halo)alkyl, hydroxy, (halo)alkoxy, -COOR7, -CONH 2, -CONHR8, -CONR7R8, -COR7, -CN, -NHR7, -NR7R8, -NR7COR8, -NR7SO 2R8, nitro, -OCOR7, -SO 3R8, -SO 2NH 2, -SO 2NHR7, -SO 2NR7R8 or (halo)alkylsulfonyl), aryloxy, arylcarbonyl or arylmethoxycarbonyl; or R2+R3 : nonaromatic ring system comprising 4-7 ring atoms of O, S, N and C (preferred); R7 : H, (cyclo)alkyl, haloalkyl, arylalkyl, hydroxyalkyl, aminoalkyl, alkoxyalkyl or (hetero)aryl (optionally substituted by 1-5 groups comprising halo, (halo)alkyl, -CN, -COOR8, -COR8, -OCOR8, nitro or (halo)alkoxy); R8 : H, (cyclo)alkyl, haloalkyl, arylalkyl, hydroxyalkyl, aminoalkyl, alkoxyalkyl or (hetero)aryl (optionally substituted by 1-5 groups comprising halo, (halo)alkyl, -CN, -COOR7, -COR7, -OCOR7, nitro or (halo)alkoxy); X ->halo, hydrogen sulfate, sulfate, tetrafluoroborate, acetate, trifluoroacetate, hexafluorophosphate, hexafluoroantimonate, anion of an aromatic 1,2-dicarboxylic acid amide or anion of an aromatic 1,2-disulfonic acid amide; and m : 0-5. [Image].