2-Chloro-3-nitro-4-pyridinecarboxylic acid

2-Chloro-3-nitro-4-pyridinecarboxylic acid Property

Boiling point:

484.7±45.0 °C(Predicted)

Density 

1.702±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

1.01±0.25(Predicted)

Appearance

Off-white to light yellow Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-Chloro-3-nitro-4-pyridinecarboxylic acid Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 2-chloro-3-nitro-4-pyridinecarboxylic acid from 2-chloro-4-methyl-3-nitropyridine: 2-chloro-4-methyl-3-nitropyridine (4.00 g, 23.00 mmol) was dissolved in sulphuric acid (40 ml) at 0 °C and potassium dichromate (8.85 g, 30.00 mmol) was added in batches. The reaction mixture was heated and stirred at 60°C for 8 hours. After completion of the reaction, the mixture was allowed to cool to room temperature and slowly poured into ice water. Multiple extractions were carried out with ethyl acetate (5 x 30 ml). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was ground with pentane (3 × 5 ml) to afford 2-chloro-3-nitro-4-pyridinecarboxylic acid (4.00 g, 19.70 mmol), which was used for subsequent reactions without further purification.LCMS analysis (Method C): 1.51 min; mass spectrometry (MS): ESI m/z 201.1 [M-1 ]; 1H NMR (400 MHz. DMSO-d6) δ 8.83 (d, J = 5Hz, 1H), 8.03 (d, J = 5Hz, 1H).

References

[1] Patent: EP2366691, 2011, A1. Location in patent: Page/Page column 7-8
[2] Patent: US2016/333009, 2016, A1. Location in patent: Paragraph 0824; 0825
[3] Patent: WO2017/93718, 2017, A1. Location in patent: Page/Page column 80