| Identification | Back Directory | [Name]
5-Hydroxy-6-nitropyridine-3-carboxylic acid | [CAS]
59288-43-6 | [Synonyms]
5-hydroxy-6-nitronicotinic acid
6-Nitro-5-hydroxy Nicotinic Acid
5-Hydroxy-6-nitropyridine-3-carboxylic acid
3-Hydroxy-2-nitro-5-pyridinecarboxylic acid
5-Hydroxy-6-nitro-3-pyridinecarboxylic acid
3-Pyridinecarboxylic acid, 5-hydroxy-6-nitro- | [Molecular Formula]
C6H4N2O5 | [MDL Number]
MFCD11044358 | [MOL File]
59288-43-6.mol | [Molecular Weight]
184.11 |
| Chemical Properties | Back Directory | [Boiling point ]
572.4±50.0 °C(Predicted) | [density ]
1.745±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [pka]
-1.53±0.10(Predicted) | [Appearance]
Light yellow to yellow Solid | [InChI]
InChI=1S/C6H4N2O5/c9-4-1-3(6(10)11)2-7-5(4)8(12)13/h1-2,9H,(H,10,11) | [InChIKey]
OODZZMDHMOPHHY-UHFFFAOYSA-N | [SMILES]
C1=NC([N+]([O-])=O)=C(O)C=C1C(O)=O |
| Hazard Information | Back Directory | [Uses]
5-Hydroxy-6-nitropyridine-3-carboxylic acid is a 5-hydroxynicotinic acid (H948565) derivative used in the preparation of aminoheteroaryl protein kinase inhibitors.
| [Uses]
A 5-hydroxynicotinic acid (H948565) derivative used in the preparation of aminoheteroaryl protein kinase inhibitors. | [Synthesis]
1. Synthesis of 6-nitro-5-hydroxynicotinic acid (B2): 5-hydroxynicotinic acid (B1) (7.0 g, 50 mmol) was dissolved in concentrated H2SO4 and 9 mL of 90% fuming HNO3 (9 mL) was added slowly. The reaction mixture was transferred to a sealed tube and the reaction was stirred at 55-60°C for 4 days. Upon completion of the reaction, the mixture was slowly poured into ice water and the pH was adjusted with 50% NaOH solution to 3. Subsequently, the aqueous phase was saturated by the addition of MgSO4 and extracted with isopropanol (4 x 45 mL). The organic phases were combined and concentrated under reduced pressure to remove the isopropanol to give 5.93 g (64% yield) of B2 as a yellow solid. The mass spectrum (APCI) showed (M + H)+ of 185. 1H-NMR (DMSO-d6) δ 8.01 (d, 1H, Ar-H), 8.41 (d, 1H, Ar-H). | [References]
[1] Patent: US2006/46991, 2006, A1. Location in patent: Page/Page column 45-46
[2] Patent: WO2006/21886, 2006, A1. Location in patent: Page/Page column 77
[3] Patent: WO2014/184234, 2014, A1. Location in patent: Page/Page column 55; 56
[4] Patent: CN105555786, 2016, A. Location in patent: Paragraph 0241 |
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J & K SCIENTIFIC LTD.
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Cool Pharm, Ltd
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