4-AMINO-3-HYDROXY PYRIDINE Chemical Properties

Melting point:

222-223°C

Boiling point:

447.4±30.0 °C(Predicted)

Density 

1.320±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

10.78±0.12(Predicted)

form 

Solid

color 

White to light brown

CAS DataBase Reference

52334-53-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HazardClass 

IRRITANT, TOXIC

HS Code 

2933399990

4-AMINO-3-HYDROXY PYRIDINE Usage And Synthesis

Uses

4-Amino-3-hydroxypyridine is a hydroxylated impurity as well as a metabolite of the potassium channel blocker Fampridine (D113500).

Definition

ChEBI: 3-Hydroxy-4-aminopyridine is an aminopyridine.

Synthesis

Example 5 Synthesis of 4-amino-3-hydroxypyridine: 3-methoxy-4-aminopyridine (200 mg, 1.6 mmol) was dissolved in dichloromethane (15 mL) under argon protection and stirred at -70°C. Boron tribromide (10 mL, 1 M solution in dichloromethane, 6 eq.) was added slowly over 10 min. After stirring under cooling conditions for 15 minutes, the reaction mixture was gradually warmed to room temperature and continued to stir overnight. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was mixed with methanol and saturated sodium bicarbonate solution and stirred for 25 minutes. The mixture was filtered and the filtrate was evaporated. The residue was stirred with a solvent mixture of dichloromethane/methanol/ammonia (75/25/2, v/v/v), filtered, and purified by silica gel column chromatography using the same solvent mixture as eluent to give 145 mg (81% yield) of the target product 4-amino-3-hydroxypyridine with a melting point of 205°C (literature value: 188°-191°C). The structure of the product was confirmed by proton NMR spectroscopy. Elemental analysis results: Calculated values (C5H6N2O-0.2H2O): C, 52.81; H, 5.67; N, 24.63. Measured values: C, 53.02; H, 5.63; N, 24.40.

References

[1] Patent: US5652363, 1997, A

4-AMINO-3-HYDROXY PYRIDINE(52334-53-9)Related Product Information

• N-(2-CHLORO-3-HYDROXYPYRIDIN-4-YL)PIVALAMIDE
• 3-HYDROXY-4-NITROPYRIDINE
• 5-Amino-2-hydroxypyridine
• 4-AMINO-PYRIDIN-2-OL
• 4-AMINO-3-HYDROXY PYRIDINE
• N-(3-HYDROXY-PYRIDIN-4-YL)-2,2-DIMETHYL-PROPIONAMIDE
• 5-Amino-2-pyridinol 1-oxide
• 2-Amino-3-hydroxypyridine
• 3-Amino-2(1H)-pyridinone
• SALOR-INT L211184-1EA
• 4-Amino-3-methoxypyridine
• 4-Amino-3-methoxy-5-nitropyridine
• 2-CHLORO-3-HYDROXY-4-NITRO-6-METHYLPYRIDINE
• 4-phenoxypyridin-3-amine
• 1H-PYRIDO[3,4-B][1,4]OXAZIN-2(3H)-ONE, 7-CHLORO-
• 1-(3-([3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]OXY)-2-METHYL-4-PYRIDINYL)-4-METHYLPIPERAZINE
• 4-AMINO-3,5-DIMETHOXYPYRIDINE
• 3-ETHOXY-4-NITROPYRIDINE