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22282-72-0

22282-72-0 Structure

22282-72-0 Structure
IdentificationMore
[Name]

2-Hydroxyisonicotinic acid
[CAS]

22282-72-0
[Synonyms]

2-HYDROXY-4-PYRIDINECARBOXYLIC ACID
2-HYDROXYISONICOTINIC ACID
2-HYDROXYPYRIDINE-4-CARBOXYLIC ACID
4-CARBOXY-2(1H)-PYRIDINONE
RARECHEM AL BO 2291
1,2-Dihydro-2-oxopyridine-4-carboxylic acid
2-HYDROXY-ISONICOTINIC ACID 98%
2-Hydroxypyridine-4-carboxylic acid, 2-Hydroxyisonicotinic acid
[EINECS(EC#)]

947-323-1
[Molecular Formula]

C6H5NO3
[MDL Number]

MFCD01318566
[Molecular Weight]

139.11
[MOL File]

22282-72-0.mol
Questions And AnswerBack Directory
[Synthesis]

90 mL of concentrated hydrochloric acid was slowly added to 5.00 g (31.7 mmol) of 2-chloroisonicotinic acid. The suspension was heated to 140-150 °C (oil bath). The resulting reaction mixture gradually became a clear solution after heating, but returned to a suspension after 24 hours. Another 20 mL of hydrochloric acid was added to the reaction system, and the mixture became clear. Heating continued for another 24 hours. Then, another 20 mL of hydrochloric acid was added, and the reaction mixture was heated for another 12 hours. The mixture was cooled in an ice bath, during which solid precipitation was observed. The reaction mixture was diluted with an equal volume of ice water and filtered. The filter cake was washed with cold water, and the precipitate was dried under high vacuum to obtain pure 2-hydroxyisonicotinic acid as a white solid, yielding 3.92 g (89%).

Synthetic Route of 2-Hydroxyisonicotinic Acid

Figure 2: Synthetic Route of 2-Hydroxyisonicotinic Acid

Chemical PropertiesBack Directory
[Melting point ]

300
[Boiling point ]

384.0±42.0 °C(Predicted)
[density ]

1.451±0.06 g/cm3(Predicted)
[storage temp. ]

Keep Cold
[form ]

Solid
[pka]

2?+-.0.20(Predicted)
[color ]

White to Orange to Green
[InChI]

InChI=1S/C6H5NO3/c8-5-3-4(6(9)10)1-2-7-5/h1-3H,(H,7,8)(H,9,10)
[InChIKey]

BXHCJLRTXPHUGH-UHFFFAOYSA-N
[SMILES]

C1(=O)NC=CC(C(O)=O)=C1
[CAS DataBase Reference]

22282-72-0(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xi
[WGK Germany ]

WGK 3
[Hazard Note ]

Irritant/Keep Cold
[HS Code ]

2933399990
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Chemical Properties]

White powder
[Uses]

Used in the synthesis of selective inhibitors of neuropeptide Y Y5 inhibiting food intake. Also used in the optimization of p-subsite residues of HIV protease inhibitors.
[Synthesis Reference(s)]

Tetrahedron Letters, 29, p. 4389, 1988 DOI: 10.1016/S0040-4039(00)80502-X
Spectrum DetailBack Directory
[Spectrum Detail]

2-Hydroxyisonicotinic acid(22282-72-0)1HNMR
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