4-Hydroxy-1,5-naphthyridine Chemical Properties

Melting point:

340 °C (sublm)

Boiling point:

332.7±22.0 °C(Predicted)

Density 

1.347±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

3.37±0.40(Predicted)

Appearance

Off-white to gray Solid

InChI

InChI=1S/C8H6N2O/c11-7-3-5-9-6-2-1-4-10-8(6)7/h1-5H,(H,9,11)

InChIKey

NSPLFNGUPLZYHV-UHFFFAOYSA-N

SMILES

N1C2C(=NC=CC=2)C(O)=CC=1

Safety Information

HS Code 

2933998090

4-Hydroxy-1,5-naphthyridine Usage And Synthesis

Uses

4-Hydroxy-1,5-Naphthidine is a heterocyclic derivative that can be used as an intermediate in organic synthesis.

Synthesis

General procedure for the synthesis of 4-hydroxy-1,5-naphthyridine (ZS96) from 2,2-dimethyl-5-((pyridin-3-ylamino)methylene)-1,3-dioxane-4,6-dione: ZS95 (100 mg, 0.403 mmol) was dissolved in diphenyl ether (3.0 mL) and refluxed for 50 min on a Bunsen burner. After completion of the reaction, the mixture was cooled to room temperature, the precipitate was collected by filtration and washed with hexane. The crude product was dried and purified by sublimation at 210 °C and 20 mbar to give white crystals ZS96 (40 mg, 68% yield).ZS96 sublimated slowly over 200 °C. IR (ATR, cm-1): 3012 (m), 2925 (s), 2855 (s), 2077 (w), 1975 (w), 1623 ( s), 1583 (m), 1559 (m), 1502 (s), 1461 (m), 1421 (m), 1328 (w), 1192 (w), 1137 (w), 1073 (w), 977 (w), 885 (w), 818 (w), 779 (w), 724 (w), 682 (w), 590 (w), 546 (w) , 481 (w).1H NMR (500 MHz, CDCl3 + d-TFA, δ): 9.15 (dd, J = 8.8, 1.2 Hz, 1H), 9.12-9.10 (m, 1H), 8.51 (d, J = 7.4 Hz, 1H), 8.41 (dd, J = 8.9, 5.4 Hz, 1H), 7.19 (d, J = 7.4 Hz, 1H). 13C NMR (125 MHz, CDCl3 + d-TFA, δ): 173.25, 147.30, 144.98, 142.03, 131.98, 131.43, 121.01, 116.06. HRMS: m/z 147.05496 [M+H]+, corresponds to molecular formula C8H6N2O (calculation error: -2.22 ppm).

References

[1] Journal of Medicinal Chemistry, 2017, vol. 60, # 4, p. 1343 - 1361
[2] European Journal of Medicinal Chemistry, 2019, p. 32 - 50

4-Hydroxy-1,5-naphthyridine(5423-54-1)Related Product Information

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