4-Chloropyridine-2-carboxamide Chemical Properties

Melting point:

148-152

Boiling point:

298.1±25.0 °C(Predicted)

Density 

1.381±0.06 g/cm3(Predicted)

storage temp. 

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

pka

14.49±0.50(Predicted)

form 

Solid

color 

Off-white

λmax

268nm(EtOH)(lit.)

InChI

InChI=1S/C6H5ClN2O/c7-4-1-2-9-5(3-4)6(8)10/h1-3H,(H2,8,10)

InChIKey

XIHHOUUTBZSYJH-UHFFFAOYSA-N

SMILES

C1(C(N)=O)=NC=CC(Cl)=C1

CAS DataBase Reference

99586-65-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2933399990

4-Chloropyridine-2-carboxamide Usage And Synthesis

Chemical Properties

4-Chloropyridine-2-carboxamide has active reactivity and special solvation ability, and can undergo dehydration, de-CO, introduction of amino groups, introduction of acyl groups, and cyclization in addition to the reaction involving three hydrogens].

Uses

4-Chloropyridine-2-carboxamide, is a versatile building block used in synthesis of various chemical compounds.

Synthesis

General procedure for the synthesis of 4-chloropyridine-2-carboxamide from 4-chloropyridine-2-carboxylic acid: a non-homogeneous mixture formed by 4-chloropyridine-2-carboxylic acid (TCI America, 5.4 g, 34.2 mmol, 1.0 equiv.) and thionyl chloride (30 mL) was heated and refluxed for 2 hr at 80 °C. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure to remove excess thionyl chloride. The resulting residue was placed in an ice bath and a methanol solution of ammonia (7 N, 45 mL) was slowly added and stirred under ice bath conditions for 15 minutes. The ice bath was then removed and the reaction mixture was allowed to gradually warm up to room temperature and stirring was continued for 3 hours. At the end of the reaction, the solvent was removed by concentration under reduced pressure and the residue was purified by recrystallization from ethyl acetate to afford the target product 4-chloropyridine-2-carboxamide (5.14 g, 96% yield) as a white solid. The product was characterized by 1H NMR (DMSO-d6): δ 8.61-8.63 (m, 1H), 8.21 (m, 1H), 8.03-8.04 (m, 1H), 7.76-7.83 (m, 2H); the mass spectrum (ESI+) showed m/z 157 ([M+H]+).

References

[1] Patent: US2005/245530, 2005, A1. Location in patent: Page/Page column 39
[2] Patent: US2007/78140, 2007, A1. Location in patent: Page/Page column 25
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 14, p. 4323 - 4329
[4] Patent: WO2014/22116, 2014, A2. Location in patent: Paragraph 0212
[5] Patent: US2015/37280, 2015, A1. Location in patent: Paragraph 0414

4-Chloropyridine-2-carboxamide(99586-65-9)Related Product Information

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