Methyl 6-methylnicotinate Chemical Properties

Melting point:

34-37 °C (lit.)

Boiling point:

160 °C/106 mmHg (lit.)

Density 

1.2023 (rough estimate)

refractive index 

1.5810 (estimate)

Flash point:

218 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

pka

3.92±0.10(Predicted)

form 

Liquid

color 

Clear colorless to slightly yellow

BRN 

122940

InChI

InChI=1S/C8H9NO2/c1-6-3-4-7(5-9-6)8(10)11-2/h3-5H,1-2H3

InChIKey

VYPPZXZHYDSBSJ-UHFFFAOYSA-N

SMILES

C1=NC(C)=CC=C1C(OC)=O

CAS DataBase Reference

5470-70-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Methyl 6-methylnicotinate Usage And Synthesis

Uses

It is used in the treatment of CNS disorders using D-amino acid oxidase and D-aspartate oxidase inhibitors.

Chemical Properties

Brown Solid

Uses

Methyl 6-methylpyridine-3-carboxylate may be used in chemical synthesis studies.

Uses

Methyl 6-methylnicotinate is used in the treatment of CNS disorders using D-amino acid oxidase and D-aspartate oxidase inhibitors.

Synthesis Reference(s)

Journal of the American Chemical Society, 97, p. 4409, 1975 DOI: 10.1021/ja00848a053

Synthesis

To a stirred solution of 6-methylpyridine-3-carboxylic acid (40 g; 290 mmol; 1 equiv.) in methanol (0.75 L) was slowly added concentrated sulfuric acid (40 mL), and the reaction mixture was heated to reflux and held for 17 hours. Upon completion of the reaction, the mixture was concentrated to dryness under reduced pressure. Subsequently, the pH of the residue was adjusted to 7 with ice-cold saturated aqueous NaHCO3 and solid NaHCO3. The aqueous layer was extracted with ethyl acetate (3 x 500 mL), the organic layers were combined, washed with saturated brine, dried with anhydrous sodium sulfate, and the solvent was removed by filtration and under reduced pressure to give methyl 6-methylnicotinate (33 g, 75% yield) as an off-white solid. The product was confirmed by 1H NMR (CDCl3): δ 9.06 (s, 1H), 8.13 (dd, 1H, J = 2,8Hz), 7.20 (d, 1H, J = 8Hz), 3.89 (s, 3H), 2.58 (s, 3H).LCMS analysis showed: m/z = 152.4 [M + H]+, retention time RT = 2.36 min (using program P1, column W).

References

[1] Patent: WO2015/95128, 2015, A1. Location in patent: Paragraph 0152; 0153; 0154
[2] Journal of Organic Chemistry, 1981, vol. 46, # 15, p. 3040 - 3048
[3] Journal of Medicinal Chemistry, 2002, vol. 45, # 23, p. 5005 - 5022
[4] Patent: WO2010/48010, 2010, A1. Location in patent: Page/Page column 35-36
[5] Patent: WO2013/128421, 2013, A1. Location in patent: Page/Page column 80

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