6-Methoxy-pyridine-2-carboxylicacidmethylester

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6-Methoxy-pyridine-2-carboxylicacidmethylester Basic information
Uses
Product Name:6-Methoxy-pyridine-2-carboxylicacidmethylester
Synonyms:Methyl 6-methoxypicolinate;2-Pyridinecarboxylic acid, 6-Methoxy-, Methyl ester;6-Methoxy-2-Pyridinecarboxylic Acid Methyl Ester;methyl 6-methoxy-2-pyridinecarboxylate;Methyl 6-methoxy;6-Methoxypyridinecarboxylic acid methyl ester;Methyl 6-methoxypyridine-2-carboxylate
CAS:26256-72-4
MF:C8H9NO3
MW:167.16
EINECS:
Product Categories:Building Blocks;C8 to C9;Chemical Synthesis;Heterocyclic Building Blocks;Pyridines
Mol File:26256-72-4.mol
6-Methoxy-pyridine-2-carboxylicacidmethylester Structure
6-Methoxy-pyridine-2-carboxylicacidmethylester Chemical Properties
Melting point 33-38℃
Boiling point 256.6±20.0 °C(Predicted)
density 1.156±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
form solid
pka0.41±0.10(Predicted)
color White
InChIInChI=1S/C8H9NO3/c1-11-7-5-3-4-6(9-7)8(10)12-2/h3-5H,1-2H3
InChIKeyQCCJUEURAZMEGY-UHFFFAOYSA-N
SMILESC1(C(OC)=O)=NC(OC)=CC=C1
Safety Information
Hazard Codes Xi
Risk Statements 37/38-41
Safety Statements 26-39
WGK Germany 3
HS Code 2933399990
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Dam. 1
Skin Irrit. 2
STOT SE 3
MSDS Information
6-Methoxy-pyridine-2-carboxylicacidmethylester Usage And Synthesis
UsesMethyl 6-methoxy-2-pyridinecarboxylate is a useful research chemical.
Synthesis Reference(s)Tetrahedron Letters, 15, p. 4339, 1974 DOI: 10.1016/S0040-4039(01)92158-6
Synthesis
6-Hydroxypicolinic acid

19621-92-2

Iodomethane

74-88-4

6-METHOXY-PYRIDINE-2-CARBOXYLICACIDMETHYLESTER

26256-72-4

General procedure for the synthesis of methyl 6-methoxypyridine-2-carboxylate from 6-hydroxypyridine-2-carboxylic acid and iodomethane: 6-hydroxypyridine-2-carboxylic acid (1 g, 7.19 mmol) and silver carbonate (2.2 g, 7.90 mmol) were placed in a round-bottomed flask, and chloroform (20 mL) was added to dissolve. Subsequently, iodomethane (1 mL, 15.81 mmol) was added slowly and dropwise. The reaction mixture was stirred at 60°C for 26 hours. After completion of the reaction, the mixture was filtered and extracted with chloroform. Next, the extract was vacuum filtered and vacuum distilled to remove the solvent. Finally, the residue was purified by column chromatography (eluent ratio of ethyl acetate: hexane = 1:5) to afford the target product methyl 6-methoxypyridine-2-carboxylate (1.25 g, 100% yield).

References[1] Patent: WO2014/3483, 2014, A1. Location in patent: Page/Page column 34
[2] Organic and Biomolecular Chemistry, 2006, vol. 4, # 6, p. 1071 - 1084
[3] Organic Letters, 2009, vol. 11, # 23, p. 5562 - 5565
[4] Patent: WO2011/79076, 2011, A1. Location in patent: Page/Page column 93
6-Methoxy-pyridine-2-carboxylicacidmethylester Preparation Products And Raw materials
Raw materials6-Hydroxypicolinic acid-->Iodomethane-->Chloroform-->Silver carbonate
Preparation Products(6-Methoxy-pyridin-2-yl)-methanol-->Methyl 1-Methyl-6-oxo-1.6-dihydropyridine-2-carboxylate
Tag:6-Methoxy-pyridine-2-carboxylicacidmethylester(26256-72-4) Related Product Information
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