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ChemicalBook--->CAS DataBase List--->93271-59-1

93271-59-1

93271-59-1 Structure

93271-59-1 Structure
IdentificationBack Directory
[Name]

2-Hydroxy-4-methylpyridine-3-carbonitrile
[CAS]

93271-59-1
[Synonyms]

3-Cyano-4-methyl-2-pyridone
2-hydroxy-4-Methylnicotinonitrile
3-Cyano-2-hydroxy-4-methylpyridine
4-methyl-2-oxo-1H-pyridine-3-carbonitrile
2-Hydroxy-4-methylpyridine-3-carbonitrile
1,2-dihydro-4-Methyl-2-oxo-3-Pyridinecarbonitrile
1,2-dihydro-4-Methyl-2-oxopyridine-3-carbonitrile
4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
3-Pyridinecarbonitrile,1,2-dihydro-4-Methyl-2-oxo-
2-Hydroxy-4-methylpyridine-3-carbonitrile ISO 9001:2015 REACH
[Molecular Formula]

C7H6N2O
[MDL Number]

MFCD00716620
[MOL File]

93271-59-1.mol
[Molecular Weight]

134.14
Chemical PropertiesBack Directory
[Melting point ]

234.7-236.1 °C
[Boiling point ]

337.7±35.0 °C(Predicted)
[density ]

1.20±0.1 g/cm3(Predicted)
[storage temp. ]

Storage temp. 2-8°C
[pka]

8.96±0.10(Predicted)
[Appearance]

Light yellow to yellow Solid
[InChI]

InChI=1S/C7H6N2O/c1-5-2-3-9-7(10)6(5)4-8/h2-3H,1H3,(H,9,10)
[InChIKey]

XSJRLWNOZDULKJ-UHFFFAOYSA-N
[SMILES]

C1(=O)NC=CC(C)=C1C#N
Safety DataBack Directory
[HS Code ]

2933399990
Spectrum DetailBack Directory
[Spectrum Detail]

2-Hydroxy-4-methylpyridine-3-carbonitrile(93271-59-1)1HNMR
Hazard InformationBack Directory
[Synthesis]

Acetylacetaldehyde dimethyl acetal

5436-21-5

2-Cyanoacetamide

107-91-5

2-Hydroxy-4-methylpyridine-3-carbonitrile

93271-59-1

Ammonium acetate (79.3 mg, 1.03 mmol) and acetic acid (0.6 mL) were added to anhydrous toluene (12.4 mL) as 4,4-dimethoxy-2-butanone (2.0 g, 15.13 mmol) and cyanoacetamide (1.6 g, 18.92 mmol) in an anhydrous toluene (12.4 mL) assembled in a Dean-Stark device and stirred and refluxed for 8 hr to remove the resulting water. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure, and the residual oily substance was cooled to room temperature and ethanol (7.0 mL) was added at 25 °C with stirring. Subsequently, 50% sulfuric acid (2.6 mL) was added slowly and the mixture was heated at 50 °C with stirring for 3 hours. After the reaction mixture was cooled to 5 °C, water (1.3 mL) was slowly added. The resulting brown solid was purified by crystallization in ethanol to give 2-hydroxy-3-cyano-4-methylpyridine (0.900 g, yield: 45%); melting point: 233-236 °C. 1H NMR (400 MHz, DMSO-d6): δ 12.58 (br s, 1H, NH), 8.04 (d, J = 7.4 Hz, 1H, H-6), 6.24 ( d, J = 7.4 Hz, 1H, H-5), 2.31 (s, 3H, CH3).

[References]

[1] European Journal of Medicinal Chemistry, 2018, vol. 154, p. 155 - 171
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