100445-95-2

Usage

Uses

Used in Pharmaceutical Industry:
N-(3-Hydroxy-2,6-diMethylphenyl)acetaMide is used as a key intermediate compound for the synthesis of Mepivacaine (M225060) metabolites. Mepivacaine is a local anesthetic drug that is widely used in medical procedures to numb specific areas of the body, providing pain relief during surgeries and other medical interventions.
Additionally, N-(3-Hydroxy-2,6-diMethylphenyl)acetaMide is used as a precursor in the preparation of pyrrolizidine derivatives, which exhibit antiarrhythmic activity. These derivatives are valuable in the development of medications aimed at treating cardiac arrhythmias, a group of conditions that affect the normal rhythm of the heart.

Upstream product

• 87-62-7 2,6-dimethylaniline 
• 2198-53-0 N-(2,6-dimethylphenyl)acetamide 
• 166541-58-8 O-(pentafluorobenzoyl)-N-acetyl-N-(2,6-dimethylphenyl)hydroxylamine 
• 167968-06-1 1,5-dimethyl-5-(benzoyloxy)-6-acetyliminocyclohexa-1,3-diene 
• 5416-12-6 N-(2,6-dimethyl-3-nitro-phenyl)acetamide 

Downstream Products

• 100445-96-3 3-amino-2,4-dimethyl-phenol 
• 1427407-02-0 tert-butyl N-(3-hydroxy-2,6-dimethylphenyl)carbamate 
• 1427407-03-1 2-fluoro-5-(3-fluorophenyl)-N-(3-hydroxy-2,6-dimethylphenyl)benzamide 
• 1427407-04-2 3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-dimethylphenol 
• 1427407-05-3 ethyl 2-[3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-dimethyl-phenoxy]acetate 
• 1427406-10-7 2-[3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]-2,4-dimethylphenoxy]acetic acid 
• 1427407-92-8 2-fluoro-5-(3-fluorophenyl)-N-(3-hydroxy-2,6-dimethylphenyl)-3-methylbenzamide 
• 1427407-93-9 3-[[2-fluoro-5-(3-fluorophenyl)-3-methylphenyl]methylamino]-2,4-dimethylphenol 
• 1427407-94-0 C₂₇H₂₉F₂NO₃ 
• 1427406-34-5 C₂₄H₂₃F₂NO₃ 
• 1427406-37-8 C₂₆H₂₇F₂NO₃ 
• 1427408-02-3 3-(3-fluorophenyl)-N-(3-hydroxy-2,6-dimethylphenyl)-5-methylbenzamide 
• 1427408-03-4 3-[[3-(3-fluorophenyl)-5-methylphenyl]methylamino]-2,4-dimethylphenol 
• 1427408-04-5 C₂₇H₃₀FNO₃ 

Relevant academic research and scientific papers

ANILINE DERIVATIVES,THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION

The present invention relates to aniline derivatives, to their preparation and to their therapeutic application.

Cyclohexadienes from the rearrangement of O-aroyl-N-acetyl-N-(2,6-dimethylphenyl)hydroxylamines. Reaction in aqueous solution to meta- and para-substituted 2,6-dimethylacetanilides

O-Aryol-N-acetyl-N-(2,6-dimethylphenyl)hydroxylamines (aroyl = benzoyl, 3-nitrobenzoyl, and pentafluorobenzoyl) rearrange in acetonitrile to 1,5-dimethyl-5-aroyloxy-6-N-acetyliminocyclohexa-1,3-dienes that can be isolated as pure compounds.These cyclohexadienes react in aqueous solutions, producing m-aroyloxy- and m-hydroxy-2,6-dimethylacetanilides in an H+-catalysed reaction and the corresponding para products in a non-catalysed reaction.Analysis of the effect of the aroyloxy group suggests that the latter reaction involves heterolysis to a reactive, non-selective, ion pair that collapses to the para product, or reacts at this position with water.The meta products arise from the N-protonated cyclohexadiene reacting with solvent in a conjugate addition to give the meta-substituted phenol, or in an intramolecular reaction with the carbonyl group to give the rearranged ester.This latter reaction is proposed to proceed via an intermediate 1,3-dioxolan-2-ylium ion.The nucleophiles azide, phenylsulfinate and the methyl thioglycolate anion react in a bimolecular fashion to give meta-substituted 2,6-dimethylacetanilides.With phenylsulfinate this requires H+, while methyl thioglycolate anion reacts with the neutral cyclohexadiene.Azide exhibits reaction by both processes.These reactions are proposed to involve conjugate additions, either to the N-protonated cyclohexadiene, or, with better nucleophiles, directly on the neutral compound.These cyclohexadienes model intermediates that may form during the metabolism of certain carcinogenic amines.These results establish the presence of three electrophilic species capable of reacting with cellular nucleophiles - the highly reactive and non-selective cation formed in the heterolysis, the less reactive and more selective N-protonated species, and the neutral cyclohexadiene itself.The last electrophile is relatively unreactive, but can be a target of very good nucleophiles such as thiol anions.

Pyrrolizidine derivative and pharmaceutical composition thereof

A novel pyrrolizidine derivative of the formula, STR1 which has potent antiarrhythmic activity and low toxicity is produced. The derivative can be synthesized: by acylating 2,6-xylidine to protect the amino group, nitrating the protected xylidine to introduce a nitro group at 3-position, reducing the nitro group to an amino group, followed by diazotizing and hydrolyzing, and then the resulted 3-hydroxy-2,6-dimethylaniline being condensed with 8-halocarbonylmethylpyrrolizidine; or by nitrating N-(2',6'-dimethyl)phenyl-8-pyrrolizidineacetamide to introduce a nitro group at 3'-position, reducing the nitro group to amino group, diazotizing the amino group and hydrolyzing the diazonium compound.