[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[CH2:15](Br)[CH3:16].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:15]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2)[CH3:16]A solution of 6-hydroxy-8-nitro-quinoline (2.5 g, 13.2 mmol), ethylbromide (1.08 mL, 14.5 mmol), and K2CO3 (4 g, 26.4 mmol) in DMF (50 mL) under a nitrogen atmosphere was heated at 40° C. for 5 hours. The cooled reaction mixture was poured into H2O (200 mL) and extracted into EtOAc (2×200 mL). The organic fractions were combined, dried over Na2SO4 and concentrated. The resulting beige solid was triturated with 40% EtOAc/hexane to give 2.46 g (85%) of the title compound as beige crystals.
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