[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[CH2:5][CH2:4][NH:3]1.C(=O)(O)[O-].[Na+].Br[CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].[I-].[K+]>C(O)C>[CH2:25]([O:24][C:22]([CH2:21][CH2:27][N:3]1[CH2:4][CH2:5][C:6]2[C:11](=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)[CH:2]1[CH3:1])=[O:23])[CH3:26]0.90 g of 1-methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline was dissolved in 20 ml of ethanol, and 1.97 g of sodium bicarbonate, 2.55 g of ethyl bromopropionate, and a catalytic amount of potassium iodide were added to the solution. The solution was heated overnight under ref lux with stirring, and extracted with ethyl acetate. After washing with water and saturated aqueous solution of sodium chloride, the solution was dried with anhydrous sodium sulfate. The desiccant was separated by filtration, and the filtrate was purified by silica gel column chromatography to obtain 0.90 g of 2-[2-(ethoxycarbonyl)ethyl]-1-methyl-7-nitro-1,2,3,4-tetrahydroisoquinoline, which was an oily product (yield: 65%).
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