2,4-DICHLORO-1,8-NAPHTHYRIDINE Chemical Properties

Melting point:

123.0 to 127.0 °C

Boiling point:

299℃

Density 

1.486

Flash point:

163℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

powder to crystal

pka

1.15±0.30(Predicted)

color 

Light yellow to Yellow to Orange

Safety Information

HS Code 

2933.99.8290

2,4-DICHLORO-1,8-NAPHTHYRIDINE Usage And Synthesis

Uses

2,4-Dichloro-1,8-diazonphthalene can be used to prepare the compound 4-chloro-1,8-diazonphthalene, which is an important intermediate in the synthesis of naphthidine derivatives. Naphthidine derivatives exert their effects by inhibiting, regulating, and/or modulating signal transduction through ATP-consuming proteins such as kinases.

Synthesis

1-Benzyl-4-hydroxy-1,8-naphthyridin-2(1H)-one (2.52 g, 10 mmol) was used as a raw material, which was dissolved in phosphoryl chloride (100 mL) and heated to reflux for 2 hours. After the reaction was completed, it was cooled to room temperature and the reaction mixture was slowly added dropwise to crushed ice while stirring. The reaction solution was neutralized with sodium hydroxide solution and subsequently extracted with ethyl acetate. The organic phase was separated, washed with saturated brine and dried over anhydrous sodium sulfate. After concentration under reduced pressure to remove the solvent, purification by column chromatography afforded 1-benzyl-4-chloro-1,8-naphthyridin-2(1H)-one (1.26 g, 47% yield) and 2,4-dichloro-1,8-diazanaphthalene (556 mg, 28% yield). 1-Benzyl-4-chloro-1,8-naphthyridin-2(1H)-one: 1H NMR (500 MHz, CDCl3) δ 8.64 (d, J = 3.0 Hz, 1H), 8.22 (d, J = 7.0 Hz, 1H), 7.49 (d, J = 7.0 Hz, 2H), 7.21-7.28 (m, 4H), 6.94 (s, 1H), 5.73 (s, 2H); 13C NMR (125 MHz, CDCl3) δ 161.62, 151.31, 149.38, 143.20, 137.49, 134.57, 128.92, 128.55, 127.58, 122.40, 118.80, 115.00, 44.56; LCMS (EI) m/z 270.9 (M+), 273.0. 2,4-Dichloro-1,8-diazanaphthalene: 1H NMR (500 MHz, CDCl3) δ 9.10 (d, J = 3.0 Hz, 1H), 8.51 (d, J = 8.5 Hz, 1H), 7.57 (dd, J = 8.5, 3.0 Hz, 1H), 7.54 (s, 1H); 13C NMR (125 MHz, CDCl3) δ 155.63, 155.39, 153.62, 144.70, 133.97, 123.38, 123.36, 120.69; LCMS (EI) m/z 198.9 (M+), 200.7, 203.0.

References

[1] Patent: WO2008/24423, 2008, A2. Location in patent: Page/Page column 43
[2] Patent: US2009/54477, 2009, A1. Location in patent: Page/Page column 18

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