Water → 1-(1-Ethylpropyl)-6-iodo-4-methyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline
Reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([I:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[C:3]=1[CH2:14][CH2:15]Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.[NH2:29][CH:30]([CH2:33][CH3:34])[CH2:31][CH3:32]>>[CH2:31]([CH:30]([N:29]1[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[C:7]([I:12])[C:6]=3[N:5]=[C:4]([CH3:13])[C:3]=2[CH2:14][CH2:15]1)[CH2:33][CH3:34])[CH3:32]Participants
5
Procedure
4-Chloro-3-(2-chloroethyl)-8-iodo-2-methylquinoline (900 mg, 2.46 mmol) was dissolved in 3-aminopentane (10 mL), followed by adding p-toluenesulfonic acid (900 mg). The mixture was sealed at 200° C. for six hours. Water was added to the reaction mixture, extracted with ethyl acetate, and the organic layer was washed with water and brine, dried over magnesium sulfate, and then evaporated. The residue was purified by silica gel column chromatography (10% ethyl acetate/hexane), to give the title compound (450 mg, 1.18 mmol) as white crystals.