Ethyl 2-aminopyridine-3-carboxylate Chemical Properties

Melting point:

96-98°C

Boiling point:

133°C/12mmHg(lit.)

Density 

1.192±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO, Methanol

pka

4.84±0.36(Predicted)

form 

Solid

color 

Yellow

InChI

InChI=1S/C8H10N2O2/c1-2-12-8(11)6-4-3-5-10-7(6)9/h3-5H,2H2,1H3,(H2,9,10)

InChIKey

KIAGEDYOPMHRRB-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

13362-26-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

29339900

Ethyl 2-aminopyridine-3-carboxylate Usage And Synthesis

Chemical Properties

Yellow Solid

Uses

A pyrimidine derivative with diuretic activity.

Synthesis

2-Aminonicotinic acid (1) (5 g, 36 mmol) and ethanol (100 mL) were used as feedstock to which concentrated sulfuric acid (10 mL) was added. The reaction mixture was heated to reflux for 16 hours and subsequently cooled to room temperature. The completion of the reaction was confirmed by LC-MS analysis. The volatiles were removed under vacuum, water was added, and the crude product was alkalized with 1N NaOH solution to pH 8.0. The product was extracted twice with ethyl acetate, and the organic phases were combined, dried over magnesium sulfate, and then concentrated to afford ethyl (2) 2-aminonicotinate (6.0 g, 100% yield) as a white crystalline solid. hplc-ms analysis results: retention time t R = 0.41 min (UV 254 nm); mass calculated value C8H10N2O2 166.1, measured value LCMS m/z 167.1 (M + H).

References

[1] Patent: WO2008/82490, 2008, A2. Location in patent: Page/Page column 70
[2] Patent: TWI525093, 2016, B. Location in patent: Page/Page column 101;
[3] Patent: WO2007/67416, 2007, A2. Location in patent: Page/Page column 64; 134
[4] Patent: WO2007/86080, 2007, A2. Location in patent: Page/Page column 37
[5] Heterocycles, 1993, vol. 36, # 11, p. 2513 - 2522

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