1-chloro-5-nitro-isoquinoline Chemical Properties

Melting point:

183-184℃

Boiling point:

376.8±27.0 °C(Predicted)

Density 

1.484

storage temp. 

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

pka

0.22±0.43(Predicted)

Appearance

Light yellow to yellow Solid

1-chloro-5-nitro-isoquinoline Usage And Synthesis

Synthesis

GENERAL METHODS: To a stirred solution of acridazine N-oxide (CAS:57554-78-6) in anhydrous dichloromethane (0.1 M) was slowly added phosphorous trichloride (1.2 eq.) at 0 °C, followed by the addition of N,N-dimethylformamide (0.5 eq.) dropwise under argon protection. The reaction mixture was gradually warmed to 25 °C and stirred continuously for several hours until thin layer chromatography (TLC) showed completion of the reaction. After completion of the reaction, saturated aqueous sodium carbonate solution was slowly added and the pH was adjusted to 7~8. The reaction mixture was separated and the aqueous phase was thoroughly extracted with dichloromethane. The organic phases were combined, washed with saturated saline, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by fast column chromatography using petroleum ether/ethyl acetate (80:1) as eluent.

References

[1] Tetrahedron Letters, 2014, vol. 55, # 51, p. 7130 - 7132

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