Methyl 4-methylnicotinate Chemical Properties

Boiling point:

57-58 °C(Press: 1-2 Torr)

Density 

1.104±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

3.86±0.18(Predicted)

form 

liquid

color 

Brown

Safety Information

HS Code 

2933399990

Methyl 4-methylnicotinate Usage And Synthesis

Uses

Methyl 4-Methylnicotinate, is an intermediate for the synthesis of various chemical compounds. It can be used for the preparation of pyridine analogs of Phthalide.

Synthesis

4-Methylpyridine-3-carboxylic acid (2.00 g, 14.6 mmol) was dissolved in methanol (50 mL) and concentrated sulfuric acid (4.66 mL, 87.6 mmol) was added. The reaction mixture was stirred at 60 °C for 16 hours. After the reaction was completed, it was concentrated under reduced pressure to remove most of the methanol. The concentrated mixture was extracted by partitioning with ethyl acetate (150 mL) and saturated aqueous sodium bicarbonate (200 mL). The organic layer was separated, dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to constant weight to give methyl 4-methylnicotinate as a clear liquid (2.30 g, 94% yield).LC/MS analysis (conditions are given in Table 2, Method a) showed a retention time of Rt = 1.67 min; mass spectrum m/z: 152 ([M+H]+).

References

[1] Patent: US2009/312338, 2009, A1. Location in patent: Page/Page column 121
[2] Tetrahedron, 2013, vol. 69, # 33, p. 6799 - 6803
[3] Journal of the American Chemical Society, 1944, vol. 66, p. 1456,1458
[4] Canadian Journal of Chemistry, 1983, vol. 61, p. 2813 - 2820
[5] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1913 - 1919

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