2-CHLORO-3-NITROPYRIDIN-4-OL Chemical Properties

Boiling point:

408.2±40.0 °C(Predicted)

Density 

1.664±0.06 g/cm3(Predicted)

storage temp. 

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

pka

-2.59±0.20(Predicted)

Appearance

Off-white to light yellow Solid

Safety Information

HS Code 

2933399990

2-CHLORO-3-NITROPYRIDIN-4-OL Usage And Synthesis

Uses

2-Chloro-3-nitropyridine-4-ol is an organic compound mainly used in organic synthesis and pesticide manufacturing, and can be used as a starting material for the synthesis of other compounds.

Synthesis

The general procedure for the synthesis of 2-chloro-3-nitro-4-hydroxypyridine from 2,4-dichloro-3-nitropyridine was as follows: 2,4-dichloro-3-nitropyridine (100 g, 518 mmol) was dissolved in N,N-dimethylformamide (500 mL) at room temperature, followed by the addition of sodium acetate (106 g, 1295 mmol). The reaction mixture was heated to 120 °C and stirred continuously for 5 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the mixture was cooled to room temperature. The reaction mixture was diluted with water (500 mL) and the pH was adjusted to less than 4 with aqueous 2N hydrochloric acid.Subsequently, the aqueous layer was extracted several times with ethyl acetate (5 x 750 mL). All organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the crude product. The crude product was further ground with water, filtered to collect the solid, and dried under vacuum to give 2-chloro-3-nitro-4-hydroxypyridine (63 g, 65% yield). Mass spectrum (ESI) m/z: 175.1 ([M+H]+); 1H NMR (400 MHz, DMSO-d6) δ: 7.10 (d, J=6.0 Hz, 1H), 8.25 (d, J=5.6 Hz, 1H), 13.10 (br s, 1H).

References

[1] Patent: WO2017/14323, 2017, A1. Location in patent: Paragraph 0247
[2] Patent: US2014/94456, 2014, A1. Location in patent: Paragraph 0713; 0715
[3] Patent: WO2015/153683, 2015, A1. Location in patent: Paragraph 0477
[4] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 20, p. 4411 - 4416
[5] Patent: US2003/225131, 2003, A1. Location in patent: Page 22

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