3-Amino-2(1H)-pyridinone Chemical Properties

Melting point:

118-130 °C

Boiling point:

206.4°C (rough estimate)

Density 

1.2111 (rough estimate)

refractive index 

1.4800 (estimate)

storage temp. 

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

form 

Powder

pka

13.87±0.10(Predicted)

color 

Dark brown to black

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C5H6N2O/c6-4-2-1-3-7-5(4)8/h1-3H,6H2,(H,7,8)

InChIKey

VTSFNCCQCOEPKF-UHFFFAOYSA-N

SMILES

C1(=O)NC=CC=C1N

CAS DataBase Reference

33630-99-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

37/39-26-36

HazardClass 

IRRITANT

HS Code 

29333999

MSDS

• Language:English Provider:ACROS

3-Amino-2(1H)-pyridinone Usage And Synthesis

Uses

3-Amino-2-hydroxypyridine has been used as a reactant in the preparation of benzothiazolyl hydroxyindolinylphenyl ureas as potent P2Y1 antagonists.

Chemical Properties

Brown to off-white crystalline powder.

Uses

It is used as pharmaceutical intermediate. It is involved in synthesis of functionalized pyrido[4,3-b][1,4]oxazine and imidazo[1,2-a]pyridine derivatives. The use of ethyl 2-chloro-3-oxopropanoate with 2-amino-3-hydroxypyridine or 3-amino-4-hydroxypyridine led, respectively, to imidazo[1,2-a]pyridine derivatives or ethyl pyrido[4,3-b][1,4] oxazine-2-carboxylate.

Synthesis

a) Synthesis of 3-aminopyridin-2-ol: In a 500 mL three-necked flask, 3-nitropyridin-2(1H)-one (1 g, 7.14 mmol) was dissolved in methanol (200 mL), followed by addition of 10% palladium/activated carbon catalyst (100 mg, 10 wt%). The reaction mixture was stirred for 3 h under hydrogen atmosphere (1 atm) and at room temperature (25°C). Upon completion of the reaction, the catalyst was removed by filtration through a diatomaceous earth pad, and the filtrate was concentrated under reduced pressure by rotary evaporator to afford the white solid product 3-aminopyridin-2-ol (800 mg, quantitative yield). Product characterization data: 1H-NMR (CD3OD, 300 MHz) δ 6.78-6.73 (m, 2H), 6.23 (t, J = 6.5 Hz, 1H); MS (ESI) m/z 111.1 [M+H]+.

References

[1] Patent: US2011/28467, 2011, A1. Location in patent: Page/Page column 14
[2] Patent: WO2006/51410, 2006, A1. Location in patent: Page/Page column 46
[3] Heterocycles, 1990, vol. 31, # 12, p. 2201 - 2204
[4] Heterocycles, 1990, vol. 31, # 12, p. 2201 - 2204
[5] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 1013,1024

3-Amino-2(1H)-pyridinone(33630-99-8)Related Product Information

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• 3-Aminopyridine
• 2-Hydroxypyridine
• 6-Aminocaproic acid
• 3-Aminophenol
• Glycine
• 2-Chloro-3-cyanopyridine
• 2-Aminopyridine
• 4-Dimethylaminopyridine
• ALTRENOGEST
• Tris(hydroxymethyl)aminomethane
• 3-Amino-5-hydroxypyridine dihydrochloride,3-AMINO-5-HYDROXYPYRIDINE
• 2-(4-FLUOROPHENOXY)-3-NITROPYRIDINE
• 5-Bromo-3-nitro-2-pyridinol
• 2-Methoxy-3-nitropyridine
• 2-Hydroxy-4-methyl-3-nitropyridine
• 3,5-DIAMINO-2,6-DIMETHOXYPYRIDINE, DIHYDROCHLORIDE SPECIALITY CHEMICALS
• 3-AMINO-2,6-DIMETHOXYPYRIDINE MONOHYDROCHLORIDE