5-Hydroxy-6-nitropyridine-3-carboxylic acid Chemical Properties

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

5-Hydroxy-6-nitropyridine-3-carboxylic acid Usage And Synthesis

Uses

5-Hydroxy-6-nitropyridine-3-carboxylic acid is 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

5-Hydroxy-6-nitropyridine-3-carboxylic acid(59288-43-6)Related Product Information

• 5-Hydroxy-6-nitropyridine-3-carboxylic acid
• 5-Hydroxynicotinic acid
• 6-NITRONICOTINIC ACID
• 2-AMINO-3-HYDROXY-5-PICOLINE