4-Hydroxy-2-methylpyridine Chemical Properties

Melting point:

174-176 °C(Solv: acetone (67-64-1))

Boiling point:

350-360 °C

Density 

1.120±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

5.36±0.18(Predicted)

Appearance

White to light yellow Solid

Safety Information

Risk Statements 

36/37/38

Safety Statements 

24/25-36/37/39

HS Code 

29339900

4-Hydroxy-2-methylpyridine Usage And Synthesis

Chemical Properties

Yellow solid

Uses

2-Methyl-4-hydroxypyridine is used in the synthesis of novel indolizine compounds as inhibitors of phosphodiesterase IV. Also used in the preparation of 2-substituted imidazole ring compoiunds for treatment againast human African trypanosomiasis.

Synthesis

General procedure for the synthesis of 4-hydroxy-2-methylpyridine from 2-methyl-4-aminopyridine: [0220] To an aqueous solution (75 mL) containing 2-methylpyridin-4-amine (10.2 g, 94 mmol) and nitric acid (56.5 mL, 1,273 mmol) was slowly added a solution of sodium nitrite solution (9.44 g, 137 mmol) in water (38 mL) over a period of 25 minutes at 0 °C while maintaining vigorous stirring. The reaction mixture was continued to be stirred at 0 °C for 30 min, followed by transfer to a refrigerator at -17 °C for overnight storage. Upon completion of the reaction, the mixture was filtered and the solid product was collected and dried under vacuum to afford 2-methylpyridin-4-ol (6.5 g, 59.6 mmol, 63.2% yield) as a beige solid. The product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 2.53-2.60 (m, 3H), 7.01-7.17 (m, 2H), 8.36-8.49 (m, 1H). Mass spectrometry analysis showed a measured value of 110.1 for [M + H]+.

References

[1] Patent: WO2011/146287, 2011, A1. Location in patent: Page/Page column 59
[2] Archiv der Pharmazie (Weinheim, Germany), 1958, vol. 291, p. 429,434
[3] Roczniki Chemii, 1957, vol. 31, p. 1147,1151
[4] Chem.Abstr., 1958, p. 10072
[5] Journal of Chemical Thermodynamics, 1982, vol. 14, # 1, p. 45 - 50

4-Hydroxy-2-methylpyridine(18615-86-6)Related Product Information

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• 4-Hydroxypyridine
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• 2-Picoline
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• 4-Methylpyridine
• Chelidamic acid
• 4-HYDROXY-2-METHYLQUINOLINE
• XANTHURENIC ACID
• KYNURENIC ACID
• 4-METHOXY-2-QUINOLINECARBOXYLIC ACID
• 2,8-Bis(trifluoromethyl)-4-quinolinol
• 6-CHLORO-4-HYDROXY-2-METHYLQUINOLINE
• 6-FLUORO-4-HYDROXY-2-METHYLQUINOLINE
• 5-CHLORO-2,8-DIMETHYL-4-QUINOLINOL