Sodium Chloride → (3,4-Dichlorobenzyl)-(8-isopropoxy-2-methylquinolin-4-yl)-amine hydrochloride

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Reaction Steps

4-(3,4-Dichlorobenzylamino)-2-methylquinolin-8-ol (example 41, 70.0 mg, 0.210 mmole) was suspended in dimethylformamide (5 mL) and mixed with sodium hydride (60% in paraffin liq., 9.24 mg). After stirring for 30 min isopropyliodide (37.5 mg, 0.221 mmole) was added dropwise and the mixture was kept under stirring at RT for 16 hrs. Diluted NaCl solution was added and the mixture was extracted with ethyl acetate. The organic phases were dried and concentrated and the residue thus obtained was purified using silica gel chromatography, eluting with dichloromethane:methanol 90:10. Precipitation in Isopropanol/iso-propyl ether/HCl gave a brownish salt (15 mg, 17%). ESI-MS [M+H]+=375.1/379.2 calculated for C20H20Cl2N2O=375 g/mole

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