Methyl 6-oxo-1,6-dihydropyridine-2-carboxylate Chemical Properties

Melting point:

109-110 °C

Boiling point:

367.6±42.0 °C(Predicted)

Density 

1.263±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

8.83±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C7H7NO3/c1-11-7(10)5-3-2-4-6(9)8-5/h2-4H,1H3,(H,8,9)

InChIKey

GJLWQAUHCDNAEK-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)NC(=O)C=CC=1

Safety Information

HS Code 

2933399990

Methyl 6-oxo-1,6-dihydropyridine-2-carboxylate Usage And Synthesis

Uses

Methyl 6-oxo-1,6-dihydropyridine-2-carboxylate, as an important pharmaceutical intermediate and fine chemical raw material, has a wide range of applications and a broad market prospect. In the pharmaceutical field, 2-pyridinemethanol, as an important pharmaceutical intermediate, can be used to synthesize bisacodyl, a blood transfusion drug, and is also a raw material for synthesizing pralidoxime, an organophosphate antidote.

Synthesis

Step 1: Synthesis of methyl 6-hydroxypyridine-2-carboxylate. 6-Hydroxypyridine-2-carboxylic acid (13.0 g, 93.5 mmol) was dissolved in methanol (150 mL) at room temperature and a dioxane solution of 4N HCl (10 mL) was slowly added. The reaction mixture was stirred at room temperature for 48 hours. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure to afford methyl 6-hydroxypyridine-2-carboxylate (13 g, 90% yield) as a white solid.

References

[1] Patent: WO2004/37808, 2004, A1. Location in patent: Page 19-20
[2] Patent: WO2014/154727, 2014, A1. Location in patent: Page/Page column 38; 52
[3] Patent: US2014/296239, 2014, A1. Location in patent: Paragraph 0097; 0098
[4] Patent: WO2014/154726, 2014, A1. Location in patent: Page/Page column 38-39
[5] Patent: US2014/296296, 2014, A1. Location in patent: Paragraph 0106; 0107

Methyl 6-oxo-1,6-dihydropyridine-2-carboxylate(30062-34-1)Related Product Information

• 5-Pyrimidinecarboxylic acid, 1,4-dihydro-4-oxo- (9CI)
• 6-OXO-1,6-DIHYDROPYRAZINE-2-CARBOXYLIC ACID
• 2-Pyridinecarboxaldehyde,1,6-dihydro-6-oxo-(9CI)