ethyl 4-amino-6-chloronicotinate Chemical Properties

Boiling point:

335.8±37.0 °C(Predicted)

Density 

1.326±0.06 g/cm3(Predicted)

storage temp. 

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

pka

2.75±0.42(Predicted)

Appearance

White to light yellow Solid

InChI

InChI=1S/C8H9ClN2O2/c1-2-13-8(12)5-4-11-7(9)3-6(5)10/h3-4H,2H2,1H3,(H2,10,11)

InChIKey

OAQIVHCEAFDMTK-UHFFFAOYSA-N

SMILES

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

ethyl 4-amino-6-chloronicotinate Usage And Synthesis

Uses

Ethyl 4-Amino-6-chloronicotinate is a useful reagent in the preparation of biologically active small molecules with pharmaceutical application.

Synthesis

Ethyl 6-chloro-4-((2,4-dimethoxybenzyl)amino)nicotinate (15 g, 42.8 mmol) was used as a raw material, which was mixed with trifluoroacetic acid (TFA, 80 mL), heated to 50 °C and the reaction was maintained for 3 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the solvent was subsequently removed under reduced pressure. The pH of the residue was adjusted to 8 with aqueous sodium bicarbonate (NaHCO3) and then extracted with ethyl acetate (EtOAc). The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated. Finally, the residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=4:1) to afford the target product ethyl 4-amino-6-chloronicotinate (5.1 g, 61% yield) as a white solid.

References

[1] Patent: WO2015/120049, 2015, A1. Location in patent: Page/Page column 218
[2] Patent: WO2014/52365, 2014, A1. Location in patent: Page/Page column 180-181

ethyl 4-amino-6-chloronicotinate(380626-81-3)Related Product Information

• Ethyl 5-broMo-6-chloropicolinate
• 3-Pyridinecarboxylic acid, 4-chloro-6-nitro-, ethyl ester
• Ethyl 6-chloro-2,4-diMethylnicotinate
• 4-Pyridinecarboxylic acid, 5-hydroxy-2-methyl-, ethyl ester
• Ethyl 6-broMo-2-chloronicotinate
• 3-Pyridinecarboxylic acid, 5-chloro-1,6-dihydro-1-methyl-6-oxo-, ethyl ester
• 5-Bromo-3-methylpyridine-2-carboxylic acid ethyl ester
• ethyl 5-chloro-3-fluoropicolinate
• Ethyl 5-bromo-2-chloroisonicotinate
• 2-Pyridinecarboxylic acid, 6-chloro-3-fluoro-, ethyl ester
• Ethyl 5-bromo-4,6-dichloronicotinate
• ethyl 4-cyano-2-pyridinecarboxylate
• ethyl 4-chloro-2-Methylnicotinate
• 3-Pyridinecarboxylic acid, 4-aMino-6-chloro-