52707-57-0

Upstream product

• 591-31-1 3-methoxy-benzaldehyde 
• 1068468-43-8 hexahydro-1,3,5-tris-(3-methoxyphenyl)-1,3,5-triazine 
• 536-90-3 m-Anisidine 
• 100-66-3 methoxybenzene 
• 100-46-9 benzylamine 
• 5071-96-5 3-METHOXYBENZYLAMINE 
• 2972-72-7 2-(3-methoxybenzylidene)malononitrile 

Downstream Products

• 591-31-1 3-methoxy-benzaldehyde 
• 5813-86-5 m-methoxybenzamide 
• 26994-69-4 3-methoxy-benzaldehyde (E)-O-(1,1-dioxo-1H-1λ⁶-benzo[d]isothiazol-3-yl)-oxime 
• 173261-51-3 [1-(3-Methoxy-phenyl)-meth-(E)-ylideneaminooxy]-acetic acid 
• 1527-89-5 3-methoxybenzonitrile 
• 161064-06-8 3-(3-Methoxy-phenyl)-5-vinyl-4,5-dihydro-isoxazole 
• 73096-36-3 5-(3-methoxyphenyl)-1H-tetrazole 

Relevant academic research and scientific papers

Modification of titanium isopropoxide with aromatic aldoximes

Dimeric [Ti(OiPr)2(benzaldoximate)2]2 was obtained upon reaction of titanium isopropoxide with two molar equivalents of benzaldehyde (E)- or (Z)-oxime or m-anisaldoxime. Two isomers were formed differing by the mutual orientation of the oximate ligands. Reaction with perillaldoxime or trans-cinnamaldoxime resulted in the corresponding derivatives with functional ligands. The degree of substitution was higher when o- or p-anisaldoxime were employed in the same molar ratio, and dimeric Ti 2(OiPr)3(o-anisaldoximate)5 with a bridging oximate ligand and monomeric Ti(oximate)4 (oximate = o-anisaldoximate or p-anisaldoximate) were obtained. Dissolution of the p-anisaldoximate derivative upon heating in [D6]DMSO led to deoximation reactions.

A mild system for synthesis of aldoximes and ketoximes in the presence of N-hydroxyphthalimide in aqueous system

An efficient method for synthesis of oximes from aldehydes or ketones with N-hydroxyphthalimide or N-hydroxysuccinimide in water has been described. It is the first time to utilize NHPI as an oximation reagent to synthesize aldoximes and ketoximes from the corresponding organic carbonyl compounds without other reagents. The reaction tolerates various functional groups and affords the corresponding oximes in 76%–98% yields. The by-product phthalic acid can be recycled from the system. In addition, this method has been successfully applied to the synthesis of the precursor of some pharmacologically active amide molecules.

CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines

This report details a general and enantioselective means for the synthesis of alkyl-substituted aziridines. This protocol offers a direct route for the synthesis of alkyl-substituted chiral aziridines from achiral starting materials. Readily accessed ally

Novel chemoenzymatic oxidation of amines into oximes based on hydrolase-catalysed peracid formation

The efficient transformation of benzylamines into the corresponding oximes has been described by means of a chemoenzymatic process. This strategy is based on a two-step sequence developed in one-pot at 30 °C and atmospheric pressure. First, the formation of a reactive peracid intermediate occurs by means of a lipase-catalysed perhydrolysis reaction, and then this peracid acts as a chemical oxidising agent of the amines. A total of nine ketoximes were isolated in high purity after a simple extraction protocol (90-98% isolated yield), while for the eleven synthesised aldoximes a further column chromatography purification was required (71-82% isolated yield). In all cases excellent selectivities were attained, offering a practical method for amine oxidation in short reaction times (1 hour). The environmental impact of the process was analysed and compared with a recently published alternative chemical synthesis, finding for this metric a good E-factor value.

METHOD FOR PRODUCING ALDOXIME COMPOUND

PROBLEM TO BE SOLVED: To provide a method for producing an aldoxime compound using no expensive catalysts and reagents and also requiring no severe reaction conditions. SOLUTION: There is provided a method for producing an aldoxime compound containing a process where an aldehyde compound and an oxime compound are brought into trans oximation reaction in the presence of perchloric acid and/or the metallic salt of perchloric acid in an organic solvent and water. The metallic salt of perchloric acid is preferably ferric perchlorate, cobalt perchlorate, nickel perchlorate, zinc perchlorate, aluminum perchlorate or calcium perchlorate. Also, the organic solvent is preferably methylene chloride and/or ethylene dichloride. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

M-CPBA mediated metal free, rapid oxidation of aliphatic amines to oximes

An efficient, rapid oxidation of various aliphatic amines to oximes using m-CPBA as an oxidant in ethyl acetate is described. High conversion (100%) with >90% oxime selectivity is achieved at room temperature under catalyst-free conditions. Mild reaction conditions along with an easy work up procedure offer lower byproduct formation and high selectivity for oximes in good yield and purity.

One-pot two-step sequential transformation: Highly efficient construction of o-2,3,5,6-tetrafluorobenzonitrile substituted oximes ethers

A practical variety of o-2,3,5,6-tetrafluorobenzonitrile substituted oximes ethers bearing broad functional groups were synthesized in moderate to good yields. The key highlight of this disclosure involving a one-pot two-step tandem procedure in aqueous media: the in situ formation of aryl aldehydes or ketones oximes followed by the SNAr reaction with pentafluorobenzonitrile via the high selective CF bond cleavage.

Selective synthesis of E-isomers of aldoximes via a domino aza-Michael/retro-Michael reaction

A highly stereoselective synthesis of E-isomer of aldoximes was developed through a basecatalysed domino aza-Michael/retro-Michael reaction of hydroxylamine and 2-(R-benzylidene)malononitrile. This reaction generates (E)-aldoxime diastereomer in high yields (eight examples, isolated yields of 82-93 %), excellent diastereomeric purity (diastereomeric ratio higher than 95 : 5 by 1H NMR), and proceeds under mild reaction conditions (aqueous NaOH, pH 12, room temperature, 4 h).

Selective synthesis of E-isomers of aldoximes via a domino aza-Michael/retro-Michael reaction

A highly stereoselective synthesis of E-isomer of aldoximes was developed through a base-catalysed domino aza-Michael/retro-Michael reaction of hydroxylamine and 2-(R-benzylidene)malononitrile. This reaction generates (E)-aldoxime diastereomer in high yie

AlPW12O40 and AlPMo12O40 as highly effective and eco-friendly catalysts for aldoximation of aldehydes under solvent-free conditions

The oxime formation of aromatic aldehydes has directly been carried out with hydroxylamine hydrochloride using heteropoly acids (AlPW12O 40, AlPMo12O40) as catalysts in the absence of solvent. It is found that these heteropoly acids were effective catalysts for the formation of oxime of aldehydes. This method consistently has the advantage of high yields of the products, short reaction time, mild and solvent-free conditions, cleaner reactions and isolation procedures.