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. Author manuscript; available in PMC: 2012 Mar 1.
Published in final edited form as: J Inorg Biochem. 2010 Sep 22;105(3):467–475. doi: 10.1016/j.jinorgbio.2010.08.011

Scheme 2.

Scheme 2

Synthesis of 1-(6-methoxyquinolin-4-yl)propan-1-ol (5, DADQQN) and 2-(diethylamino)-1-(6-methoxyquinolin-4-yl)ethanol (8, DQQN): i) SeO2, 4:1 dioxane/H2O, 90°C, 15 h, 70%; ii) EtMgBr, THF, 0°C, 6 h, 57% yield; iii) MeNO2, Et3N, MeOH, −10°C, 5 h, 66%; iv) LiAlH4, THF, 0°C to rt, 1 h, 35%; (v) EtI, Et3N, DMF, rt, 24 h, 18%.