105151-48-2

Basic information

• Product Name: 5-Methylpyridine-2,3-dicarboxylatediethylester
• Synonyms: 5-Methylpyridine-2,3-dicarboxylatediethylester;Diethyl 5-Methylpyridine-2,3-dicarboxylate
• CAS NO: 105151-48-2
• Molecular Formula: C₁₂H₁₅NO₄
• Molecular Weight: 0
• Mol File: 105151-48-2.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-Methylpyridine-2,3-dicarboxylatediethylester(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methylpyridine-2,3-dicarboxylatediethylester(105151-48-2)
• EPA Substance Registry System: 5-Methylpyridine-2,3-dicarboxylatediethylester(105151-48-2)

Safety Data

• Hazardous Substances Data: 105151-48-2(Hazardous Substances Data)

Usage

General Description

5-Methylpyridine-2,3-dicarboxylatediethylester is a chemical compound whose primary feature consists of a pyridine ring, a six-membered aromatic compound containing one nitrogen atom. The pyridine ring is substituted with a methyl group at the 5th position and two dicarboxylate ester groups at the 2nd and 3rd positions. The dicarboxylate ester groups consist of two ester functionalities, which are commonly seen in fat molecules and other biologically active compounds. 5-Methylpyridine-2,3-dicarboxylatediethylester can be relevant in various chemical reactions and syntheses due to its unique structure. The precise properties and potential applications would depend on the compound's overall reactivity and behavior in a specific chemical environment.

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

Downstream Products

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

Relevant articles and documents

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.

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 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.