METHYL 6-OXO-1,6-DIHYDRO-3-PYRIDINECARBOXYLATE Chemical Properties

Melting point:

166-170°C

Boiling point:

342.4±42.0 °C(Predicted)

Density 

1.263±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

9.99±0.10(Predicted)

form 

powder to crystal

color 

White to Light yellow

InChI

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

InChIKey

JTVVPKLHKMKWNN-UHFFFAOYSA-N

SMILES

C1NC(=O)C=CC=1C(OC)=O

CAS DataBase Reference

66171-50-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant/Keep Cold

HazardClass 

IRRITANT

HS Code 

2933399990

METHYL 6-OXO-1,6-DIHYDRO-3-PYRIDINECARBOXYLATE Usage And Synthesis

Synthesis Reference(s)

Journal of the American Chemical Society, 104, p. 1428, 1982 DOI: 10.1021/ja00369a049
Organic Syntheses, Coll. Vol. 4, p. 532, 1963

Synthesis

General procedure for the synthesis of methyl 6-hydroxynicotinate from methanol and 6-hydroxynicotinic acid: first, 6-hydroxynicotinic acid (100 g, 719 mmol) was suspended in methanol (1 L). Subsequently, 18 M sulfuric acid (50 mL) was added and the reaction mixture was heated to reflux for 16 hours. Upon completion of the reaction, the reaction mixture was cooled and sodium bicarbonate powder (45 g) was slowly added to partially neutralize the acidity. Next, most of the methanol was evaporated under reduced pressure. Water (1 L) was added to the residue and the pH was adjusted to 7 by careful addition of sodium bicarbonate solution. the suspension was extracted with dichloromethane (4 x 200 mL), the organic phases were combined and dried over anhydrous sodium sulfate. After removing the solvent under reduced pressure, the resulting solid was dried in a vacuum oven at 50 °C for 1.5 h to give 83 g (75% yield) of methyl 6-hydroxynicotinate as a white solid. Mass spectrum (electrospray ionization): 154.2 (MH+, C7H7NO3). 1H NMR (300 MHz, CDCl3): δ 3.88 (s, 3H), 6.59 (dd, 1H), 8.02 (dd, 1H), 8.21 (m, 1H), 13.19 (bs, 1H).

References

[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6679 - 6703
[2] Patent: WO2012/52444, 2012, A1. Location in patent: Page/Page column 12
[3] Chemistry - A European Journal, 2009, vol. 15, # 24, p. 5950 - 5955
[4] Patent: WO2009/106885, 2009, A1. Location in patent: Page/Page column 296
[5] Organic and Biomolecular Chemistry, 2010, vol. 8, # 15, p. 3534 - 3542

METHYL 6-OXO-1,6-DIHYDRO-3-PYRIDINECARBOXYLATE(66171-50-4)Related Product Information

• 6-oxo-1,6-dihydropyridine-3-carboxylic acid hydrazide
• Ethyl 6-Hydroxyhexanoate
• 6-HYDROXYHEXANOIC ACID METHYL ESTER
• 6-HYDROXYNICOTINIC ACID ETHYL ESTER
• 6-BROMO-4-INDAZOLECARBOXYLIC ACID METHYL ESTER
• Methyl 6-bromonicotinate
• METHYL 6-FORMYLNICOTINATE
• methyl 6-chloropyrimidine-4-carboxylate
• Methyl 6-bromoisoquinoline-1-carboxylate
• Methyl 6-bromohexanoate
• Methyl 6-chloronicotinate
• 6-CHLORO-2-PICOLINIC ACID METHYL ESTER
• METHYL 6-CHLOROPYRIDAZINE-3-CARBOXYLATE
• methyl 6-methylpyridine-2-carboxylate
• 6-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER
• Methyl 6-bromo-2-naphthoate
• 6-METHYLPYRAZINE-2-CARBOXYLIC ACID METHYL ESTER
• 2-Chloro-6-pyrazinecarboxylic acid methyl ester