Water → 1-(1-Ethylpropyl)-6-iodo-4-methyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline

반응식

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]

참가 물질

반응물 4

HCID 962Water

HCID 6101p-Toluenesulfonic acid

HCID 120193-Pentanamine

HCID 222495054-Chloro-3-(2-chloroethyl)-8-iodo-2-methylquinoline

생성물 1

HCID 222499561-(1-Ethylpropyl)-6-iodo-4-methyl-2,3-dihydro-1H-pyrrolo[3,2-c]quinoline

실험 절차

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.