4-METHYL-6-NITRO-QUINOLIN-2-OL synthesis

Yield:90771-17-8 92%

Reaction Conditions:

with sulfuric acid;nitric acid at 20; for 2 h;Cooling with ice;

Steps:

31 4.1.31 4-Methyl-6-nitroquinolin-2-ol (47)

4-methylquinolin-2-ol (46) (3.0g, 18.9mmol) was dissolved in 10ml concentrated sulfuric acid, then mixed acid (1.4ml 65% HNO3+1.4ml concentrated sulfuric acid) was dropped in ice bath. The mixture was stirred at rt for 2h. After confirming the reaction was finished, the mixture was slowly dropped into 100ml ice water and vigorously stirred. The precipitate was filtered off, washed with water and dried to give 47 as a yellow solid (3.6g, 92.0%). ¹H NMR (300MHz, DMSO-d₆) δ 12.16 (brs, 1H), 8.50 (s, 1H), 8.33 (dd, J=9.0, 2.5Hz, 1H), 7.44 (d, J=9.3Hz, 1H), 6.56 (s, 1H), 2.50 (s, 3H).

References:

Jiang, Fen;Guo, An-ping;Xu, Jia-cheng;Wang, Hui-Jie;Mo, Xiao-fei;You, Qi-Dong;Xu, Xiao-Li [European Journal of Medicinal Chemistry,2017,vol. 141,p. 1 - 14]