2,4-Dichloropyridine-3-carboxylic acid Chemical Properties

Melting point:

166-167°

Boiling point:

325.2±37.0 °C(Predicted)

Density 

1.612±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

0.79±0.25(Predicted)

color 

White to Almost white

InChI

InChI=1S/C6H3Cl2NO2/c7-3-1-2-9-5(8)4(3)6(10)11/h1-2H,(H,10,11)

InChIKey

ZFGZNVSNOJPGDV-UHFFFAOYSA-N

SMILES

C1(Cl)=NC=CC(Cl)=C1C(O)=O

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

2,4-Dichloropyridine-3-carboxylic acid Usage And Synthesis

Chemical Properties

off-white powder

Uses

2,4-Dichloropyridine-3-carboxylic Acid is useful for the preparation of prolyl hydroxylase inhibitors or erythropoietin inducing agents.

Synthesis

GENERAL STEPS: A THF solution (28.4 mL, 56.8 mmol) of 2M lithium diisopropylammonium (LDA) was slowly added to a tetrahydrofuran (THF, 70 mL) solution of 2,4-dichloropyridine (7 g, 47.3 mmol) at -78 °C, maintaining the temperature at -78 °C and stirring for 30 min. Upon completion of the reaction, the reaction mixture was quenched with excess dry ice, followed by warming to room temperature and continued stirring for 30 min. After neutralizing the reaction mixture with 1.5 N hydrochloric acid (HCl), it was diluted with ethyl acetate (100 mL) and washed sequentially with saturated brine (2 x 50 mL) and deionized water (100 mL). The organic layer was separated, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to afford 2,4-dichloronicotinic acid (4.5 g, 23.44 mmol, 50% yield) as a brown solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 8.47 (d, 1H), 7.74 (d, 1H).

References

[1] Patent: WO2016/149393, 2016, A1. Location in patent: Paragraph 0426
[2] Patent: US2011/77267, 2011, A1. Location in patent: Page/Page column 27
[3] European Journal of Organic Chemistry, 2001, # 7, p. 1371 - 1376
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 1, p. 386 - 390
[5] Patent: WO2015/116060, 2015, A1. Location in patent: Page/Page column 92

2,4-Dichloropyridine-3-carboxylic acid(262423-77-8)Related Product Information

• 2-Chloro-5-chloromethylpyridine
• 3,4-Dichloropyridine
• 3-Hydroxypyridine
• 2,4-Dichloropyridine
• 6-Chloronicotinic acid
• Quinclorac
• 2-Picolinic acid
• 2-Chloro-3-cyanopyridine
• 2-Chloronicotinic acid
• Chromium picolinate
• 4-Chloronicotinic acid
• 5-Chloronicotinic acid
• 1,2-Dichloroethane
• Dichloroethane
• Sodium dichloroisocyanurate
• Thionyl chloride
• N,N-Dimethylacetamide
• 3-Aminopyridine