3-AMINO-ISONICOTINIC ACID METHYL ESTER Chemical Properties

Melting point:

84-86

Boiling point:

292.5±20.0 °C(Predicted)

Density 

1.238±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

4.05±0.18(Predicted)

color 

White to Yellow to Green

InChI

InChI=1S/C7H8N2O2/c1-11-7(10)5-2-3-9-4-6(5)8/h2-4H,8H2,1H3

InChIKey

XLQIGLBALJNHKR-UHFFFAOYSA-N

SMILES

C1=NC=CC(C(OC)=O)=C1N

CAS DataBase Reference

55279-30-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/38

Safety Statements 

24/25

Hazard Note 

Irritant

HS Code 

29333990

3-AMINO-ISONICOTINIC ACID METHYL ESTER Usage And Synthesis

Chemical Properties

Yellow powder

Uses

3-Aminoisonicotinic Acid Methyl Ester is a useful synthetic intermediate. It is used in the synthesis of morpholinophenylquinazolines and related derivatives as PI3 kinase p110α inhibitors. It is also used to synthesize aryl tetrahydropyridine inhibitors of farnesyltransferase as antitumor agents.

Synthesis

3-Aminoisonicotinic acid (3.55 g, 25.7 mmol) was added with concentrated sulfuric acid (2.5 ml) and methanol (50 ml), and the reaction was heated to reflux at 80°C for 3 days. After completion of the reaction, methanol was removed by evaporation and the residue was diluted with deionized water (75 ml) and heated to 80 °C. Solid sodium carbonate was added slowly until no gas was produced. The reaction mixture was cooled to room temperature and extracted with dichloromethane (2 x 100 ml). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated to give methyl 3-aminoisonicotinate as a beige solid (2.36 g, 60% yield). The product was characterized by 1H NMR (500 MHz, DMSO-d6): δ 8.24 (1H, s), 7.74 (1H, d, J=5.3 Hz), 7.46 (1H, d, J=5.2 Hz), 6.67 (2H, brs), 3.83 (3H, s). The mass spectrum (ES+) showed the molecular ion peak m/z 153 ([M+H]+).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 7, p. 1359 - 1362
[2] Patent: WO2005/49613, 2005, A1. Location in patent: Page/Page column 38
[3] Patent: WO2008/74749, 2008, A1. Location in patent: Page/Page column 62-63
[4] Chemical Communications, 2016, vol. 52, # 59, p. 9283 - 9286

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