2-Amino-4-chloro-6-picoline Chemical Properties

Melting point:

108-109 °C

Boiling point:

245.1±35.0 °C(Predicted)

Density 

1.260±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

5.96±0.35(Predicted)

color 

Grey

InChI

InChI=1S/C6H7ClN2/c1-4-2-5(7)3-6(8)9-4/h2-3H,1H3,(H2,8,9)

InChIKey

IKKMKJOVXQEEHS-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

36340-61-1

Safety Information

HS Code 

2933399990

2-Amino-4-chloro-6-picoline Usage And Synthesis

Synthesis

The general procedure for the synthesis of 2-amino-4-chloro-6-methylpyridine from 2-amino-4,6-dichloropyridine and trimethylcyclotriboroxane is as follows: to a 10% aqueous solution of dioxane (0.1 M) were added sequentially 2-amino-4,6-dichloropyridine (1.0 eq.), trimethylcyclotriboroxane (1.5 eq.), tetrakis(triphenylphosphine)palladium (0.10 eq.) and potassium carbonate (3.0 eq.). The reaction mixture was heated to 120 °C in an oil bath with continuous stirring for 18 hours. Upon completion of the reaction, it was cooled to room temperature (note: not all ingredients were completely consumed). The reaction mixture was extracted with ethyl acetate and the organic phase was dried over anhydrous sodium sulfate and subsequently concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 5% methanol/dichloromethane as eluent, resulting in an off-white 2-amino-4-chloro-6-methylpyridine solid in 23% yield.LCMS analysis showed a molecular ion peak (m/z) of 143 (MH+) for the target compound with a retention time (Rt) of 1.11 min on the liquid chromatogram.

References

[1] Patent: US2011/195980, 2011, A1. Location in patent: Page/Page column 15