Acetone → 6-Bromo-2,2,4-trimethyl-1,2-dihydroquinoline

반응식

[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.S([O-])([O-])(=O)=O.[Mg+2].II.C1([C:19](=[CH:21][CH:22]=[CH:23][CH:24]=1)O)O.[CH3:25]C(C)=O>>[Br:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][CH:3]=1)[NH:6][C:23]([CH3:24])([CH3:25])[CH:22]=[C:21]2[CH3:19]

참가 물질

반응물 5

HCID 180Acetone

HCID 289Catechol

HCID 807Iodine

HCID 78074-Bromoaniline

HCID 24083Sulfuric acid magnesium salt (1:1)

생성물 1

HCID 107294646-Bromo-2,2,4-trimethyl-1,2-dihydroquinoline수율 27%

실험 절차

4-Bromoaniline (50 g, 0.290 mol), magnesium sulfate (250 g, 2 mol), iodine (2.5 g, 0.01 mol) and catechol (2.24 g, 0.020 mol) were combined in acetone (750 mL) in a sealed-tube reaction flask. The reaction vessel was placed in a pre-equilibrated oil bath set at 125° C. and stirred overnight. The reaction mixture was then cooled to room temperature, filtered over a pad of diatomaceous earth, and concentrated in vacuo. Chromatography on silica gel provided 6-bromo-2,2,4-trimethyl-1,2-dihydroquinoline as tan colored crystals (21 g, 27% yield).