105151-48-2

Usage

Uses

Used in Chemical Synthesis:
5-Methylpyridine-2,3-dicarboxylatediethylester is used as a synthetic intermediate for the production of various chemical compounds. Its unique structure allows it to participate in a range of reactions, making it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Methylpyridine-2,3-dicarboxylatediethylester is used as a building block for the development of new drugs. Its reactivity and structural features enable the creation of novel molecular entities with potential therapeutic applications.
Used in Material Science:
5-Methylpyridine-2,3-dicarboxylatediethylester is employed as a component in the development of advanced materials, such as polymers and composites. Its incorporation into these materials can impart specific properties, such as improved stability or enhanced functionality, depending on the desired application.
Used in Research and Development:
5-Methylpyridine-2,3-dicarboxylatediethylester is utilized as a research compound in academic and industrial laboratories. Its unique structure and reactivity make it an interesting subject for studies aimed at understanding chemical reactions, exploring new synthetic pathways, and discovering potential applications in various fields.

Synthetic route

5-methyl-pyridine-2,3-dicarboxylic acid (53636-65-0) + ethanol (64-17-5) → diethyl 5-methylpyridine-2,3-dicarboxylate (105151-48-2)

Conditions	Yield
With sulfuric acid; toluene-4-sulfonic acid In benzene at 75℃;	98%
With sulfuric acid at 110℃; for 1h; Temperature;

4-H-5-methyl-1-(p-methoxyphenyl)pyridine-2,3-dicarboxylic acid diethyl ester → diethyl 5-methylpyridine-2,3-dicarboxylate (105151-48-2)

Conditions	Yield
With ammonium cerium (IV) nitrate In water; acetonitrile at 20℃; for 2h; Solvent;	91.21%

diethyl N-cyclohexylamino-butenedioate + methylacrolein oxime (73502-59-7) → diethyl 5-methylpyridine-2,3-dicarboxylate (105151-48-2)

Conditions	Yield
In 1,2-dichloro-ethane	62%

methylacrolein oxime (73502-59-7) + diethyl (Z)-2-(morpholino)-2-butenedioate (116308-60-2) → diethyl 5-methylpyridine-2,3-dicarboxylate (105151-48-2)

Conditions	Yield
In 1,2-dichloro-ethane	40%

2-methylpropenal (78-85-3) + diethyl 2-aminomaleate (86319-87-1) → diethyl 5-methylpyridine-2,3-dicarboxylate (105151-48-2)

Conditions	Yield
In acetic acid
With formic acid In water

diethyl 5-methylpyridine-2,3-dicarboxylate (105151-48-2) + triethylamine (121-44-8) → [(5,6-dicarboxy-3-pyridyl)methyl]triethylamine ammonium bromide diethyl ester

Conditions	Yield
Stage #1: diethyl 5-methylpyridine-2,3-dicarboxylate With sodium bromate; 2,2'-azobis(isobutyronitrile); sodium hydrogensulfite In water; ethyl acetate at 60 - 70℃; for 8h; Inert atmosphere; Stage #2: triethylamine at 20℃; for 4h; Temperature;	59.1%

diethyl 5-methylpyridine-2,3-dicarboxylate (105151-48-2) + azobisisobutyronitrile (34241-39-9) + 5-methyl-2,3-pyridinedicarboxylic acid dimethyl ester (112110-16-4) → [(5.6-Dicarboxy-pyridin-3-yl)methyl]tri-methylammonium bromide

Conditions	Yield
With N-Bromosuccinimide; trimethylamine In chlorobenzene

diethyl 5-methylpyridine-2,3-dicarboxylate (105151-48-2) + 2-amino-2,4-dimethylbutyramide → (RS)-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-methylnicotinic acid

Conditions	Yield
With potassium tert-butylate In water; toluene

diethyl 5-methylpyridine-2,3-dicarboxylate (105151-48-2) → diethyl 5-(methoxymethyl)-2,3-pyridinedicarboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: N-Bromosuccinimide / 1 h 2: 0.5 h / 0 °C 3: sodium hydroxide / 1 h View Scheme

diethyl 5-methylpyridine-2,3-dicarboxylate (105151-48-2) → 5-bromomethylpyridine-2,3-dicarboxylic acid diethyl ester

Conditions	Yield
With N-Bromosuccinimide for 1h; Time;
With 2,2'-azobis(isobutyronitrile); bromine In 1,2-dichloro-ethane at 80℃; for 2h;

diethyl 5-methylpyridine-2,3-dicarboxylate (105151-48-2) → [(5,6-dicarboxy-3-pyridyl)methyl]triethylamine ammonium bromide diethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / 1 h 2: 0.5 h / 0 °C View Scheme

diethyl 5-methylpyridine-2,3-dicarboxylate (105151-48-2) → C15H23N2O4(1+)*Br(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine; 2,2'-azobis(isobutyronitrile) / 1,2-dichloro-ethane / 2 h / 80 °C 2: 5 h / 20 °C / 4560.31 Torr View Scheme

diethyl 5-methylpyridine-2,3-dicarboxylate (105151-48-2) → 5-(methoxymethyl)-2,3-pyridinedicarboxylic acid (143382-03-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: bromine; 2,2'-azobis(isobutyronitrile) / 1,2-dichloro-ethane / 2 h / 80 °C 2: 5 h / 20 °C / 4560.31 Torr 3: sodium hydroxide / methanol / 15 h / 80 °C View Scheme

diethyl 5-methylpyridine-2,3-dicarboxylate (105151-48-2) → 5-methyl-pyridine-2,3-dicarboxylic acid (53636-65-0)

Conditions	Yield
With sodium hydroxide In water at 20 - 80℃; for 5h;	75 g

diethyl 5-methylpyridine-2,3-dicarboxylate (105151-48-2) + 2-amino-2,3-dimethylbutyramide (40963-14-2) → C14H17N3O3

Conditions	Yield
With palladium dichloride In toluene at 70℃; for 2h; Solvent; Temperature; Reagent/catalyst; Inert atmosphere;

Upstream product

• 78-85-3 2-methylpropenal 
• 86319-87-1 diethyl 2-aminomaleate 
• 53636-65-0 5-methyl-pyridine-2,3-dicarboxylic acid 
• 64-17-5 ethanol 
• 73502-59-7 methylacrolein oxime 
• 116308-60-2 diethyl (Z)-2-(morpholino)-2-butenedioate 

Downstream Products

• 143382-03-0 5-(methoxymethyl)-2,3-pyridinedicarboxylic acid 
• 112110-16-4 5-methyl-2,3-pyridinedicarboxylic acid dimethyl ester 
• 53636-65-0 5-methyl-pyridine-2,3-dicarboxylic acid 
• 81334-60-3 (RS)-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-methylnicotinic acid 

Relevant academic research and scientific papers

Preparation method of 5-alkyl substituted pyridine-2,3-diformate diester compound

The invention provides a preparation method of a 5-alkyl substituted pyridine-2,3-diformate diester compound. Pyridine dicarboxylic acid, alcohol, an acid catalyst and a solvent are added into a reactor and heated to carry out reactions; water diversion is performed through rectification, wherein the addition amount of alcohol is 4-10 times of that of pyridine dicarboxylic acid (mole number), andthe addition amount of acid is 1-6 times of that of pyridine dicarboxylic acid (proton mole number). The preparation method is simple in process flow, high in product content and high in yield. Moreover, by controlling the process conditions, no byproduct is generated basically, the raw materials can be recycled repeatedly, and the three-waste pollution is small.

A kind of preparation method of the herbicide intermediates imidazolinones

The present invention belongs to the field of organic synthesis, and particularly relates to a method for preparing an imidazolinone weed killer intermediate. According to the present invention, the imidazolinone weed killer intermediate preparation reaction formula is as the follow, and a compound 1 is adopted as a raw material and reacts in a polar solvent through ceric ammonium nitrate to obtain an intermediate, ie., 5-methylpyridine-2,3-dicarboxylic acid diester or 5-methoxymethylpyridine-2,3-dicarboxylic acid diester, wherein R1 is methyl or methoxymethyl, and R2 is methyl or ethyl; and the method has characteristics of simple reparation process, simple operation and easily available raw materials, and is the method for easily preparing a large amount of the imidazolinone weed killer intermediate 5-methyl or 5-methoxymethyl pyridine-2,3-dicarboxylic acid diester.

Synthesis method of 5-methoxy methyl pyridine-2,3-diethyl phthalate

The invention discloses a synthesis method of 5-methoxy methyl pyridine-2,3-diethyl phthalate and belongs to the technical field of organic chemical synthesis.The synthesis method comprises the steps that 5-picoline-2,3-dicarboxylic acid is used as a raw material, firstly the 5-picoline-2,3-dicarboxylic acid and absolute ethyl alcohol react to generate 5-picoline-2,3-diethyl phthalate, then N-bromo succinimide is added, further 5-brooethyl pyridine-2,3-diethyl phthalate is generated, then triethylamine and methyl alcohol are dropwise added to the 5-brooethyl pyridine-2,3-diethyl phthalate for nucleophilic substitution reaction, a 5-methoxy methyl pyridine-2,3-diethyl phthalate solution is obtained after reaction, and the 5-methoxy methyl pyridine-2,3-diethyl phthalate is obtained through liquid separation, chromatographic column separation and reduced pressure distillation.The synthesis method is simple and easy to operate, and the synthesis yield is remarkably improved and is as high as 91%.

Process for preparing pyridine and quinoline derivatives

The present invention pertains to a method of preparing substituted and unsubstituted N-hydroxy-2-aminobutane diacid derivatives which can be dehydrated to 2-aminobut-2-ene dioic acid derivatives, which can be subsequently converted to pyridine and quinoline derivatives.

Process for the preparation of dialkyl 2,3-pyridinedicarboxylate and derivatives thereof from an α,β-unsaturated oxime and an aminobutenedioate

There is provided a convenient process for the preparation of commercially useful pyridinedicarboxylate compounds by the condensation of an α, β-unsaturated oxime and an aminomaleate or aminofumarate or mixtures thereof.

Process for preparing pyridine-2,3-dicarboxylic acid compounds

A process for preparing pyridine-2,3-dicarboxylic acid compounds of the following formula, which comprises preparing α-halo-oxalacetic acid diesters by reacting oxalacetic acid diester alkali metallic salts with an acid and a halogenating agent or by reacting oxalic acid diesters with halo-acetic acid esters, and then reacting the obtained α-halo-oxalacetic acid diesters with 2-propenal compounds and ammonia. STR1 wherein R1 and R2 are, identical or different, a lower alkyl group, and R3 is a hydrogen atom or a lower alkyl group. The pyridine-2,3-dicarboxylic acid componds obtained by the process of the ivention are useful as an intermediate for manufacturing agricultural chemicals and pharmaceuticals.

Process for preparing pyridine-2,3-dicarboxylic acid compounds

A process for preparing pyridine-2,3-dicarboxylic acid compounds of the following formula: STR1 wherein R1 and R3 are, identical or different, each a hydrogen atom or a lower alkyl group, R2 is a hydrogen atom, a lower alkyl group, or a phenyl-(lower)alkyl group which may have halogen atom or lower alkyl group on its phenyl ring, and R4 and R5 are, identical or different, each a lower alkoxy group. The compounds are useful as an intermediate for preparing agricultural chemicals and pharmaceuticals.