Hydrogen chloride-ethyl acetate → 3-methoxy-N-(4-methoxybutyl)-2-nitroaniline
Reaction equation
C(OC(=O)[N:7]([CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH3:24])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=1[N+:16]([O-:18])=[O:17])(C)(C)C.C(OCC)(=O)C.Cl>C(OCC)(=O)C>[CH3:15][O:14][C:10]1[C:9]([N+:16]([O-:18])=[O:17])=[C:8]([CH:13]=[CH:12][CH:11]=1)[NH:7][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH3:24]Participants
4
Procedure
tert-Butyl(4-methoxybutyl)(3-methoxy-2-nitrophenyl)carbamate (2.11 g) was dissolved in ethyl acetate (30 ml), 4M hydrogen chloride-ethyl acetate (15 ml) was added, and the mixture was stirred for 12 hr. The reaction mixture was concentrated under reduced pressure, diluted with saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, concentration under reduced pressure to give the object product (1.50 g).