Ethyl (6-aminopyridin-2-yl)acetate Chemical Properties

Boiling point:

298.7±25.0 °C(Predicted)

Density 

1.168±0.06 g/cm3(Predicted)

storage temp. 

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

pka

5.84±0.24(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C9H12N2O2/c1-2-13-9(12)6-7-4-3-5-8(10)11-7/h3-5H,2,6H2,1H3,(H2,10,11)

InChIKey

AJIPGVQKXQFJNX-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2933399990

Ethyl (6-aminopyridin-2-yl)acetate Usage And Synthesis

Synthesis

General procedure for the synthesis of ethyl (6-aminopyridin-2-yl)acetate from ethyl [6-[(tert-butoxycarbonyl)amino]-2-pyridinyl]acetate: to a solution of ethyl [6-[(tert-butoxycarbonyl)amino]-2-pyridinyl]acetate (1.38 g, 4.92 mmol) in methylene chloride (20 ml), was added a solution of dioxane in 4 M HCl (4 equiv. 19.7 mmol) and the reaction mixture was stirred at room temperature for 4 hours. Subsequently, 4 equivalents of dioxane solution of 4M HCl was added additionally and stirring was continued for 16 hours. Upon completion of the reaction, the mixture was concentrated in vacuum to afford the crude product ethyl (6-aminopyridin-2-yl)acetate (1.20 g, yield >100%, containing about 14% of the feedstock). Analysis by LC/MS showed a product purity of about 75% (MH+, m/z 181, retention time Rt=0.68 min). The resulting product does not require further purification and can be used directly in subsequent reactions.

References

[1] Patent: WO2006/50908, 2006, A1. Location in patent: Page/Page column 32; 39-40

Ethyl (6-aminopyridin-2-yl)acetate(71469-82-4)Related Product Information

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