3,4-Dinitrophenol → 4-(3,4-Dinitro-phenoxy)-quinoline

Reaktionsgleichung

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[N+:12]([C:15]1[CH:16]=[C:17]([OH:24])[CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])([O-:14])=[O:13]>C(Cl)Cl.[OH-].[Na+]>[N+:12]([C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[O:24][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1)([O-:14])=[O:13]

Komponenten

Versuchsvorschrift

4-Chloroquinoline (4.3 g, 26.3 mmol) and 3,4-dinitrophenol (41.5 g, 24.4 mmol) were heated at 150° C. for 30 min. The mixture was cooled to RT and the residue was dissolved in CH2Cl2. The mixture was diluted in NaOH 2 M and extracted with CH2Cl2. The organic phase was dried, filtered and evaporated. The residue was diluted in EtOAc and filtered through a silica pad. The solvent was removed to give the title compound as a brown solid.