21182-01-4

Upstream product

• 100-39-0 benzyl bromide 
• 25108-37-6 potassium pyridine-4-carboxylate 
• 100-44-7 benzyl chloride 
• 39178-35-3 isonicotinoyl chloride hydrochloride 
• 100-51-6 benzyl alcohol 
• 55-22-1 pyridine-4-carboxylic acid 
• 108-88-3 toluene 
• 586-95-8 pyridine-4-methanol 
• 107622-88-8 4-benzyloxymethylpyridine 

Downstream Products

• 112981-43-8 1-methyl-4-benzyloxycarbonylpyridinium iodide 
• 36209-51-5 4-amino-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 

Relevant academic research and scientific papers

Combined Iron/Hydroxytriazole Dual Catalytic System for Site Selective Oxidation Adjacent to Azaheterocycles

This report details a new method for site-selective methylene oxidation adjacent to azaheterocycles. A dual catalysis approach, utilizing both an iron Lewis acid and an organic hydroxylamine catalyst, proved highly effective. We demonstrate that this method provides complementary selectivity to other known catalytic approaches and represents an improvement over current heterocycle-selective reactions that rely on stoichiometric activation.

Convenient esterification of carboxylic acids by SN2 reaction promoted by a protic ionic-liquid system formed in situ in solvent-free conditions

The reaction of esterification of benzoic acid with benzyl chloride was chosen as a model reaction to study the esterification by SN2 promoted by tertiary amine as deprotonating agent. The use of ionic liquid (IL) 1,3-dimethylimidazolium methanesulfonate [MMIm][OMs] as reaction medium has proven to give quantitative yield of the ester, but interestingly the reaction does occur even in solvent-free conditions, where the acid + the amine form a liquid system (a protic IL) in situ. This last methodology was extended to several carboxylic acids in conditions of atom economy (i.e., without excess of any reagent), giving moderately good yields of esters (54-78%) recovered by weight in pure form.

Phosphorus oxychloride as an efficient coupling reagent for the synthesis of esters, amides and peptides under mild conditions

A mild method is described for the conversion of carboxylic acids into esters, amides, as well as peptides without racemization through carboxyl activation by the reagent combination of POCl3 and DMAP. Long chain alcohols could be converted to the corresponding ester in good yields. 31P NMR spectrum was used to detect phosphorus-containing intermediates in ongoing reactions directly, and a possible mechanism has been proposed based on these results. The Royal Society of Chemistry 2013.

An expedient esterification of aromatic carboxylic acids using sodium bromate and sodium hydrogen sulfite

Treatment of aromatic carboxylic acids and substituted toluenes with a mixture of sodium bromate and sodium hydrogen sulfite in a two-phase system gave the corresponding esters in good yield. The intermediate α-brominated toluene was formed by the in situ generated hypobromous acid. The α-bromotoluene underwent an intermolecular nucleophilic substitution reaction with aromatic carboxylic acids present in the reaction mixture to afford the corresponding esters.

HYDROLYSIS OF N-METHYLNICOTINYL AND N-METHYLISONICOTINYL ESTERS AND SOME n-PARTICIPATING DERIVATIVES UNDER MICELLAR CONDITIONS

Hydrolysis rate of two types of compounds, A and B were studied in the presence of variable concentrations of an anionic surfactant (sodium dodecylsulfate, SDS).Class A of compounds consists of substances which hydrolyze by the SN1 mechanism and which are

CONVENIENT SYNTHESIS OF ESTERS OF 2-PYRROLECARBOXYLIC ACID AND OF PYRIDINECARBOXYLIC ACIDS BY SOLID-LIQUID PHASE TRANSFER CATALYSIS WITHOUT ADDED SOLVENT

By reaction of aromatic K-carboxylates having nucleophilic N-atom in solid-liquid phase transfer catalysis (PTC) conditions without added solvent (catalyst : tetraalkylammonium halide) with alkylating reagents, the corresponding esters are prepared.By a judicious choice of experimental conditions, the amounts of N-alkylated products can be lowered.From 2-pyrrolecarboxylic acid, the three isomers of pyridinecarboxylic acid and o-aminobenzoic acid, corresponding esters of ethyl, benzyl, n-octyl and n-cetyl, generally are obtained with good yields.