4-CHLORO-6-NITROQUINAZOLINE Chemical Properties

Melting point:

128 °C

Boiling point:

380.0±22.0 °C(Predicted)

Density 

1.566±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

Dichloromethane

form 

Solid

pka

0.14±0.50(Predicted)

color 

Brown

CAS DataBase Reference

19815-16-8

4-CHLORO-6-NITROQUINAZOLINE Usage And Synthesis

Chemical Properties

Brown Solid

Uses

Intermediate in the preparation of anticancer agents and enzyme inhibitors.

Synthesis

Step 1: Synthesis of 4-chloro-6-nitroquinazoline To a solution of toluene (200 mL) containing 6-nitroquinazolin-4-ol (9.00 g, 47.1 mmol) and triethylamine (TEA, 9.53 g, 94.2 mmol) was slowly added phosphorus oxychloride (POCl3, 5.2 mL, 56.8 mmol) at 25 °C. Subsequently, the reaction mixture was heated to 80 °C and stirred at this temperature for 3.0 hours. Upon completion of the reaction, the mixture was cooled to 25 °C and diluted with the addition of toluene (100 mL). The organic phase was separated, washed with ice water (50 mL), dried over anhydrous sodium sulfate (Na2SO4), filtered, and concentrated by decompression to afford the title compound 4-chloro-6-nitroquinazoline as a yellow solid (7.00 g, 64.2% yield). The structure of the compound was confirmed by the following spectral data: 1H NMR (400 MHz, DMSO-d6) δ: 8.78 (s, 1H), 8.54 (d, J = 6.8 Hz, 1H), 8.39 (s, 1H), 7.87 (d, J = 12.4 Hz, 1H).

References

[1] Patent: CN108373452, 2018, A. Location in patent: Paragraph 0010; 0024; 0036-0041; 0050-0053
[2] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 12, p. 3974 - 3980
[3] Chinese Journal of Chemistry, 2014, vol. 32, # 6, p. 538 - 544
[4] Patent: WO2014/177038, 2014, A1. Location in patent: Paragraph 00255-00256
[5] Tetrahedron Letters, 2012, vol. 53, # 6, p. 674 - 677

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