2-CHLORO-7-NITROQUINOXALINE synthesis

Yield: 96%

Reaction Conditions:

with trichlorophosphate for 3 h;Reflux;

Steps:

Procedure for the synthesis of 2-chloro-7-nitroquinoxaline(4)
In a round bottom flask, a mixture of 7-nitroquinoxalin-2-ol (3) (12.73 g, 67 mmol) in 20 mL of phosphoryl chloride(POCl3) was refluxed for 3 h. Then, the mixture wasslowly poured into a stirred mixture of ice and water. Theprecipitate was filtrated and washed with water to obtain13.43 g of a red/cherry solid. Yield 96%; mp 183-186 °C(lit. 185-189 °C);5 ATR/FTIR ν / cm-1 3092, 3048, 1682,1525, 1350, 740; 1H NMR (200 MHz, DMSO-d6) δ 9.22(s, 1H, H3), 8.88 (d, 1H, J 3.0, H8), 8.59 (dd, 1H, J 2.0, 9.0, H6), 8.39 (d, 1H, J 9.0, H5); 13C NMR (100 MHz,DMSO-d6) δ 149.2, 148.8, 148.3, 142.8, 140.2, 130.9,124.1, 123.9; DEPT-135 (100 MHz, DMSO-d6) δ 148.8,130.9, 124.1, 123.9; MS 209.1 + 211.1.

References:

Do Amaral, Daniel N.;De Sá Alves, Fernando R.;Barreiro, Eliezer J.;Laufer, Stefan A.;Lima, Lídia M. [Journal of the Brazilian Chemical Society,2017,vol. 28,# 10,p. 1874 - 1878]