2050-22-8

Basic information

• Product Name: Diethyl pyridine-2,3-dicarboxylate
• Synonyms: DIETHYL 2,3-PYRIDINEDICARBOXYLATE;Diethyl pyridine-2,3-dicarboxylate;2,3-Pyridinedicarboxylic acid diethyl ester;Diethyl 2,3-quinolinate;Diethyl 3,4-pyridinecarboxylate;2,3-diethyl pyridine-2,3-dicarboxylate;2,3-Bis(ethoxycarbonyl)pyridine
• CAS NO: 2050-22-8
• Molecular Formula: C₁₁H₁₃NO₄
• Molecular Weight: 223.23
• Mol File: 2050-22-8.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 295.8 °C at 760 mmHg
• Flash Point: 132.7 °C
• Appearance: /
• Density: 1.165 g/cm³
• Vapor Pressure: 0.00149mmHg at 25°C
• Refractive Index: 1.508
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: -0.55±0.10(Predicted)
• CAS DataBase Reference: Diethyl pyridine-2,3-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl pyridine-2,3-dicarboxylate(2050-22-8)
• EPA Substance Registry System: Diethyl pyridine-2,3-dicarboxylate(2050-22-8)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 2050-22-8(Hazardous Substances Data)

Usage

Uses

Diethyl Pyridine-2,3-dicarboxylate is a useful reagent in preparation of herbicides.

InChI:InChI=1/C11H13NO4/c1-3-15-10(13)8-6-5-7-12-9(8)11(14)16-4-2/h5-7H,3-4H2,1-2H3

Synthetic route

Pyridine-2,3-dicarboxylic acid (89-00-9) + ethanol (64-17-5) → 2,3-diethyl pyridinedicarboxylate (2050-22-8)

Conditions	Yield
With toluene-4-sulfonic acid at 100℃; for 120h;	91.8%
With sulfuric acid at 100℃; for 12h; Sealed tube;	90%
With sulfuric acid at 19℃; for 17.5h; Fischer esterification; Reflux; Inert atmosphere; Large scale reaction;	78%

2,3-dichloro-pyridine (2402-77-9) + ethanol (64-17-5) + carbon monoxide (201230-82-2) → 2,3-diethyl pyridinedicarboxylate (2050-22-8)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; sodium acetate; palladium diacetate at 160℃; under 11250.9 Torr; for 3h; Carboxylation;	85%

acetylenedicarboxylic acid diethyl ester (762-21-0) + Propargylamine (2450-71-7) → 2,3-diethyl pyridinedicarboxylate (2050-22-8)

Conditions	Yield
With dihydrogen peroxide In ethanol at 65℃; for 12h; Temperature;	82%

aminodiester + acrolein monomer + diethyl 2-aminofumarate (36016-13-4) → 2,3-diethyl pyridinedicarboxylate (2050-22-8)

Conditions	Yield
With toluene-4-sulfonic acid In butan-1-ol	72.3%

acrolein monomer + diethyl 2-aminofumarate (36016-13-4) → 2,3-diethyl pyridinedicarboxylate (2050-22-8)

Conditions	Yield
With toluene-4-sulfonic acid In butan-1-ol	72.3%

C11H15NO4 → 2,3-diethyl pyridinedicarboxylate (2050-22-8)

Conditions	Yield
In nitrobenzene at 190℃; for 5h; Green chemistry;	56%

ethanol (64-17-5) + quinolinic acid α-ethyl ester-β chloride → 2,3-diethyl pyridinedicarboxylate (2050-22-8)

ethanolic HCl + Pyridine-2,3-dicarboxylic acid (89-00-9) → 2,3-diethyl pyridinedicarboxylate (2050-22-8)

Conditions	Yield
With hydrogenchloride; toluene-4-sulfonic acid In EtOAC; ethanol

oxalyl dichloride (79-37-8) + concentrated NH4 OH + NH4 OCOCH3 + ethyl vinyl ether (109-92-2) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) + diethyl oxaloacetate (108-56-5) → 2,3-diethyl pyridinedicarboxylate (2050-22-8)

Conditions	Yield
With hydrogenchloride; acetic acid; triethylamine In ethanol; water; 1,2-dichloro-ethane

2,3-pyridinedicarboxylic acid chloride (55155-23-2) + ethanol (64-17-5) → 2,3-diethyl pyridinedicarboxylate (2050-22-8)

Conditions	Yield
for 1h; Reflux;

Pyridine-2,3-dicarboxylic acid (89-00-9) → 2,3-diethyl pyridinedicarboxylate (2050-22-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / 2 h / Reflux 2: 1 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: acetic anhydride / 4 h / 115 °C 2: sulfuric acid / 16 h / Reflux View Scheme

Pyridine-2,3-dicarboxylic anhydride (699-98-9) + ethanol (64-17-5) → 2,3-diethyl pyridinedicarboxylate (2050-22-8)

Conditions	Yield
With sulfuric acid for 16h; Reflux;	11.39 g

2,3-diethyl pyridinedicarboxylate (2050-22-8) + methyl iodide (74-88-4) → 2,3-diethoxycarbonyl-1-methylpyridinium iodide (1381866-76-7)

Conditions	Yield
at 20℃; for 96h;	87%

2,3-diethyl pyridinedicarboxylate (2050-22-8) → 1-oxy-pyridine-2,3-dicarboxylic acid diethyl ester (114526-80-6)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃;	77%
With sulfuric acid; dihydrogen peroxide; acetic acid In dichloromethane

2,3-diethyl pyridinedicarboxylate (2050-22-8) + succinic acid diethyl ester (123-25-1) → diethyl 5,8-dihydroxyquinoline-6,7-dicarboxylate (39713-32-1)

Conditions	Yield
With sodium ethanolate In ethanol; toluene Heating / reflux;	77%
With sodium ethanolate In ethanol; toluene at 16 - 80℃; Claisen condensation; Inert atmosphere; Large scale reaction;
With sodium ethanolate In ethanol

2,3-diethyl pyridinedicarboxylate (2050-22-8) + bis(pinacol)diborane (73183-34-3) → C17H24BNO6

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 8-([2,2'-bipyridin]-5-yl)quinolin-2(1H)-one; potassium tert-butylate In tetrahydrofuran at 80℃; for 12h; Reagent/catalyst; Glovebox; Sealed tube; regioselective reaction;	72%

1-[(4-fluorophenyl)methyl]-2,5-pyrrolidinedione (86386-65-4) + 2,3-diethyl pyridinedicarboxylate (2050-22-8) → 7-(4-fluoro-benzyl)-5,9-dihydroxy-pyrrolo[3,4-g]quinoline-6,8-dione (684284-29-5)

Conditions	Yield
With sodium methylate In tetrahydrofuran for 24h; Dieckmann condensation; Heating;	66%
With sodium hydride In tetrahydrofuran; methanol for 24h; Heating / reflux;	66%

2,3-diethyl pyridinedicarboxylate (2050-22-8) → pyridine-2,3-dicarbaldehyde (4663-93-8) + 2-formyl-3-pyridinecarboxylic acid ethyl ester (21908-07-6)

Conditions	Yield
With diisobutylaluminium hydride In hexane; toluene at -70℃; for 0.333333h;	A 16.5% B 37.5%

dichloromethane (75-09-2) + 2,3-diethyl pyridinedicarboxylate (2050-22-8) → 2-formyl-3-pyridinecarboxylic acid ethyl ester (21908-07-6)

Conditions	Yield
In diisobutylaluminium hydride; ethyl acetate; toluene	36.8%

2,3-diethyl pyridinedicarboxylate (2050-22-8) → 7H-furo[3,4-b]pyridin-5-one (5657-51-2)

Conditions	Yield
With sodium tetrahydroborate; calcium chloride In ethanol at 0℃; for 2.5h;	25%

2,3-diethyl pyridinedicarboxylate (2050-22-8) + 2-(Diethylamino)ethanol (100-37-8) → pyridine-2,3-dicarboxylic acid bis-(2-diethylamino-ethyl ester)

Conditions	Yield
With sodium 2-(diethylamino)ethanolate under 70 Torr;

2,3-diethyl pyridinedicarboxylate (2050-22-8) → 2,3-bis(chloromethyl)-pyridine (45754-12-9)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether Erwaermen des Reaktionsprodukts mit Thionylchlorid;

2,3-diethyl pyridinedicarboxylate (2050-22-8) → d,l-cis-piperidine-2,3-dicarboxylic acid,diethyl ester (99319-04-7)

Conditions	Yield
With nickel; methyl cyclohexane at 100℃; under 110326 - 220652 Torr; Hydrogenation;
With nickel kieselguhr-catalyst; methyl cyclohexane at 150℃; under 110326 - 220652 Torr; Hydrogenation;
With 1,4-dioxane; nickel at 125℃; under 110326 - 220652 Torr; Hydrogenation;

octanol (111-87-5) + 2,3-diethyl pyridinedicarboxylate (2050-22-8) → 2-octyl-3-ethyl pyridinedicarboxylate

Conditions	Yield
With 4 A molecular sieve In di-isopropyl ether at 60℃; for 240h;	90 % Chromat.

2,3-diethyl pyridinedicarboxylate (2050-22-8) → 2,3-Lutidine (583-61-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium alanate; diethyl ether / Erwaermen des Reaktionsprodukts mit Thionylchlorid 2: palladium/calcium carbonate; methanol / Hydrogenation View Scheme

CH2l2radient + 2,3-diethyl pyridinedicarboxylate (2050-22-8) → 2-formyl-3-pyridinecarboxylic acid ethyl ester (21908-07-6)

Conditions	Yield
With diisobutylaluminium hydride In EtOAC; toluene

2,3-diethyl pyridinedicarboxylate (2050-22-8) + potassium tert-butylate (865-47-4) + 3,3,3-trifluoro-2-amino-2-methylpropionamide (122008-12-2) → 2-(5-methyl-5-trifluoromethyl-1H-imidazol-4-on-2-yl)pyridine-3carboxylic acid (122007-89-0)

Conditions	Yield
In water; toluene

silver nitrate (AgNO3) + ammonium peroxydisulphate (NH4)2 S2 O8 + 2,3-diethyl pyridinedicarboxylate (2050-22-8) + sulfuric acid (7664-93-9) + cyclopropanecarboxylic acid (1759-53-1) → 6-cyclopropyl-pyridine-2,3-dicarboxylic acid diethyl ester

Conditions	Yield
In water

2,3-diethyl pyridinedicarboxylate (2050-22-8) → Pyridine-2,3-dicarboxylic acid (89-00-9)

Conditions	Yield
With sodium acetate; acetic anhydride In water

2,3-diethyl pyridinedicarboxylate (2050-22-8) + 2-amino-2,3-dimethylbutyramide (40963-14-2) → potassium salt of 2-(5-isopropyl-5-methyl-4-oxoimidazolin-2-yl)-3-pyridinecarboxylic acid (81334-38-5)

Conditions	Yield
With potassium tert-butylate In toluene

Upstream product

• 2402-77-9 2,3-dichloro-pyridine 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 79-37-8 oxalyl dichloride 
• 109-92-2 ethyl vinyl ether 
• 68-12-2 N,N-dimethyl-formamide 
• 108-56-5 diethyl oxaloacetate 
• 36016-13-4 diethyl 2-aminofumarate 
• 699-98-9 Pyridine-2,3-dicarboxylic anhydride 
• 89-00-9 Pyridine-2,3-dicarboxylic acid 
• 55155-23-2 2,3-pyridinedicarboxylic acid chloride 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 
• 2450-71-7 Propargylamine 

Downstream Products

• 45754-12-9 2,3-bis(chloromethyl)-pyridine 
• 21908-07-6 2-formyl-3-pyridinecarboxylic acid ethyl ester 
• 89-00-9 Pyridine-2,3-dicarboxylic acid 
• 5657-51-2 7H-furo[3,4-b]pyridin-5-one 
• 7596-64-7 6-Hydroxychinolinsaeure 
• 583-61-9 2,3-Lutidine 
• 684284-29-5 7-(4-fluoro-benzyl)-5,9-dihydroxy-pyrrolo[3,4-g]quinoline-6,8-dione 
• 4663-93-8 pyridine-2,3-dicarbaldehyde 

Relevant articles and documents

Structure of 2,3-dicarboxy-1-methylpyridinium chloride studied by X-ray diffraction, DFT calculation, NMR, FTIR and Raman spectra

The structure of 2,3-dicarboxy-1-methylpyridinium chloride (1) has been studied by X-ray diffraction, DFT calculations, NMR, FTIR and Raman spectra. The crystals are monoclinic, space group P21/c. Chloride anion links two 2,3-dicarboxy-1-methylpyridinium cations into infinite zigzag chains down the [0 0 1] direction by the OH?Cl-?HO hydrogen bonds of 2.970(2) and 3.011(2) ?. Hydrogen bond lengths in single molecules (2-4) optimized by the B3LYP/6-311++G(d,p) approach depend on the environment and intramolecular O·H·O hydrogen bond. Linear correlations between the experimental 13C and 1H chemical shifts (δexp) of the investigated compound in DMSO-d6 and the GIAO/B3LYP/6-311++G(d.p) magnetic isotropic shielding constants (σcalc) calculated using the screening solvation model (COSMO), δexp = a + b σcalc, are reported. The FTIR spectrum of the solid compound is consistent with the X-ray structure. The deformation in-plane and out-of-plane OH vibrations, both in FTIR and second-derivative (d2) spectra, appear as two bands consistent with the OH?Cl-?HO arrangement.

Transition-Metal-Free Synthesis of Pyridine Derivatives by Thermal Cyclization of N -Propargyl Enamines

A transition-metal-free synthesis of pyridine derivatives by 6- endo - dig cyclization of N -propargyl enamines was developed. This method is environmentally friendly and is a high atom economy reaction that is easily accessed to provide pyridine derivatives in moderate to good yield by heating N -propargyl enamines in solvent without additives. The total synthesis of onychine was achieved in 51% yield in only two steps by using this method.

Pyridine -2,3-di-carboxylic acid ethyl ester preparation method

The invention discloses a preparation method of diethylpyridine-2,3-dicarboxylate. The preparation method comprises the step that propargylamine and diethyl acetylenedicarboxylate, which are taken as raw materials, react in an organic solvent with hydrogen peroxide as an oxidizing agent, thus finally obtaining diethylpyridine-2,3-dicarboxylate, wherein the reaction temperature is 60-70 DEG C; the reaction time is 11-13 hours; the mole ratio of propargylamine to diethyl acetylenedicarboxylate to hydrogen peroxide is 1 to 1 to (1.4-1.6); the organic solvent is ethanol. Diethylpyridine-2,3-dicarboxylate prepared by adopting the method has the technical advantages of high yield, low production cost, low environmental pollution, and the like.