5-METHOXY-PYRIDIN-2-YLAMINE Chemical Properties

Melting point:

36-38 °C

Boiling point:

128-1300C/10Torr

Density 

1.139±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform, Dichloromethane

form 

Oil

pka

3.57±0.10(Predicted)

color 

Dark Red

InChI

InChI=1S/C6H8N2O/c1-9-5-2-3-6(7)8-4-5/h2-4H,1H3,(H2,7,8)

InChIKey

XJKJHILCYUUVSJ-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(OC)C=C1

Safety Information

HS Code 

2933399990

5-METHOXY-PYRIDIN-2-YLAMINE Usage And Synthesis

Chemical Properties

Dark Red Oil

Synthesis

General procedure for the synthesis of 2-amino-5-methoxypyridine from 2-bromo-3-methoxy-6-nitropyridine: 2-bromo-3-methoxy-6-nitropyridine (1.20 g, 5.15 mmol), hydrazine hydrate (6 mL), Pd/C (10%, 400 mg), and ethanol (40 mL) were mixed and heated to reflux for 45 minutes. Upon completion of the reaction, the mixture was allowed to cool and filtered through Celite. The filtrate was concentrated, water (20 mL) and saturated ammonia (10 mL) were added and extracted with chloroform (2 x 50 mL). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated to give 2-amino-5-methoxypyridine as a colorless solid with a low melting point. Yield: 615 mg (96%).1H NMR (DMSO-d6, 400MHz) δ 7.64 (dd, 1H), 7.10 (dd, 1H), 6.42 (dd, 1H), 5.43 (br.s, 2H), 3.68 (s, 3H).

References

[1] Patent: WO2007/51981, 2007, A1. Location in patent: Page/Page column 57
[2] Patent: WO2007/51982, 2007, A1. Location in patent: Page/Page column 49
[3] Pharmazie, 2000, vol. 55, # 12, p. 907 - 912
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 3, p. 637 - 645
[5] Australian Journal of Chemistry, 1981, vol. 34, # 4, p. 927 - 932

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