3-Pyridinecarboxamide,2-amino-(9CI) Chemical Properties

Melting point:

194-200 °C

Boiling point:

328.2±22.0 °C(Predicted)

Density 

1.323±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

14.60±0.50(Predicted)

form 

Solid

color 

Pale yellow

InChI

InChI=1S/C6H7N3O/c7-5-4(6(8)10)2-1-3-9-5/h1-3H,(H2,7,9)(H2,8,10)

InChIKey

HTPCDVLWYUXWQR-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36-43

Safety Statements 

26-36/37

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

HazardClass 

6.1

HS Code 

29333990

3-Pyridinecarboxamide,2-amino-(9CI) Usage And Synthesis

Synthesis

The general procedure for the synthesis of 2-aminopyridine-3-carboxamide from 2-aminonicotinic acid was as follows: 2-aminonicotinic acid (1.38 g, 10.0 mmol) was suspended in DMF (50 mL) and HOBt (1.35 g, 10.0 mmol), NH4Cl (1.07 g, 20.0 mmol), EDC-HCl (2.88 g, 15.0 mmol) and triethylamine (2.78 mL, 20.0 mmol). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was removed by distillation under reduced pressure and CH2Cl2 (150 mL) and saturated aqueous NaHCO3 solution (150 mL) were added to the residue. The organic phase was separated, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by rapid chromatography on silica gel (3→5% MeOH-CH2Cl2) to afford 2-aminopyridine-3-carboxamide (1.21 g, 8.85 mmol, 89% yield) in white powder form. The product was characterized by 1H NMR (DMSO-d6) and ESI-MS: 1H NMR (DMSO-d6) δ: 6.55 (1H, dd, J = 7.7,4.8 Hz), 7.17 (2H, s), 7.30 (1H, s), 7.92 (2H, dd, J = 7.7,1.8 Hz), 8.06 (1H, dd, J = 4.8, 1.8 Hz); ESI-MS. 1.8 Hz); ESI-MS m/z: 138 (M + H)+.

References

[1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 5, p. 1623 - 1642
[2] Medicinal Chemistry Research, 2011, vol. 20, # 4, p. 408 - 420
[3] Synthesis, 1998, # 10, p. 1467 - 1475
[4] Patent: WO2018/125961, 2018, A1. Location in patent: Page/Page column 103; 104
[5] Monatshefte fuer Chemie, 1900, vol. 21, p. 963

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