2-METHYL-5-NITRONICOTINIC ACID Chemical Properties

Melting point:

215-215.5 °C

Boiling point:

370.1±42.0 °C(Predicted)

Density 

1.477±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

2.47±0.10(Predicted)

Appearance

Light brown to brown Solid

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

2-METHYL-5-NITRONICOTINIC ACID Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-methyl-5-nitronicotinic acid from ethyl 2-methyl-5-nitronicotinate: compound D4 (300 g, 1.4 mol) was dissolved in a mixture of 800 mL hydrochloric acid and 800 mL water. The reaction mixture was heated under reflux conditions for 1 hour. Upon completion of the reaction, it was cooled to room temperature, the reaction solution was diluted with 2.0 L of water and slowly neutralized with the addition of solid sodium bicarbonate to pH=5.0. During this process, a precipitate was gradually formed. The mixture was further cooled and the precipitate was collected by filtration. After drying, brown solid D5 (223 g, 85.7% yield) was obtained. The product was characterized by 1H NMR (DMSO-d6, 300 MHz): δ = 2.84 (s, 3H), 8.74-8.75 (d, 1H), 9.35-9.36 (d, 1H), 13.90 (s, 1H).LC-MS analysis showed that the [M-1]+ peak was located at 180.9.

References

[1] Patent: WO2008/88881, 2008, A1. Location in patent: Page/Page column 33-34
[2] Journal of the American Chemical Society, 1953, vol. 75, p. 737
[3] Patent: WO2007/56016, 2007, A2. Location in patent: Page/Page column 105

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