Sulfuric Acid → 6-Bromo-7-methylquinoline

反応式

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[CH3:9].[N+]([C:13]1[CH:18]=CC=C[CH:14]=1)([O-])=O.S(=O)(=O)(O)O>C(O)C(O)CO>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[CH3:9])[N:8]=[CH:18][CH:13]=[CH:14]2

参加物

実験手順

A mixture of 20 g of 4-bromo-3-methyl-phenylamine, 6.6 g of ferrous sulfate, 40.8 g of propane-1,2,3-triol, 8.12 g of nitrobenzene and 23 ml of concentrated sulfuric acid were heated gently. After the first vigorous reaction, the mixture was heated to reflux for 3 h and then evaporated to remove the excess nitrobenzene. To the solution was added saturated NaHCO3 to pH 8 and the solution was filtered and extracted with dichloromethane. The dichloromethane layers were combined and dried over Na2SO4 and concentrated. The solid was purified via flash column chromatography to give yellow solid which was washed with petroleum ether to return the title compound (7.5 g, 65%). NMR (CDCl3, 300 MHz) δ 8.89 (m, 1H), 8.04 (m, 2H), 7.96 (s, 1H), 7.36 (m, 1H), 2.60 (s, 3H).