8-CHLORO-[1,7]NAPHTHYRIDINE Chemical Properties

Boiling point:

307.9±22.0 °C(Predicted)

Density 

1.349±0.06 g/cm3(Predicted)

storage temp. 

2-8°C, stored under nitrogen

pka

1.54±0.30(Predicted)

Appearance

White to off-white Solid

Safety Information

HS Code 

2933998090

8-CHLORO-[1,7]NAPHTHYRIDINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 8-chloro-1,7-naphthyridine from 1,7-naphthyridin-8(7H)-one: 1,7-naphthyridin-8(7H)-one (2.0 g, 13.7 mmol) was dissolved in phosphorus triclopyr (20 mL) and heated and refluxed at 100 °C for 16 h. The progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure to remove the solvent. The residue was neutralized by adding saturated sodium bicarbonate solution (20 mL) and subsequently extracted with ethyl acetate (3 x 25 mL). The organic phases were combined, washed with saturated saline (25 mL) and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the resulting crude product was purified by silica gel column chromatography to afford 8-chloro-1,7-naphthyridine (1.4 g, 62% yield) using dichloromethane/methanol (98:2 to 95:5, v/v) as eluent. Mass spectrum (EI) m/z: 165.3 ([M+H]+); 1H NMR (400 MHz, DMSO-d6) δ: 7.64 (d, J = 6.0 Hz, 1H), 7.70 (dd, J = 4.0, 8.4 Hz, 1H), 8.22 (dd, J = 1.6, 8.4 Hz, 1H), 8.40 (d, J = 6.0 Hz. 1H), 9.15 (dd, J = 1.6, 4.0 Hz, 1H).

References

[1] Patent: WO2017/14323, 2017, A1. Location in patent: Paragraph 0280

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