[OH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[C:7]([O:14][CH3:15])[CH:6]=2.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H-].[Na+].CN1CCCN(C)C1=O>C1COCC1>[CH2:16]([O:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[C:7]([O:14][CH3:15])[CH:6]=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1To 3-hydroxy-6,7-dimethoxyquinoline (150 mg; 0.73 mmol) in 3 mL THF is added benzyl bromide (0.13 mL; 188 mg; 1.10 mmol) and Nail (59 mg; 1.46 mmol). This is stirred at room temperature for 1 hour and 25 mg of NaH added followed by 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU)(255 mg; 2.07 mmol) and stirred at room temperature for 31/2 hours. The reaction mixture is partitioned between EtOAc and distilled H2O and extracted 2× with EtOAc. The latter is washed with brine, dried (MgSO4), filtered, evaporated to dryness and chromatographed with 1% MeOH/CHCl3 to obtain 3-benzyloxy-6,7-dimethoxyquinoline m.p. 146.5°-148.5° C.).
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