C(N=[CH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[C:10]2Cl)CCC.[CH3:18][O:19][CH2:20][CH2:21][O-:22].[Na+].C[O:25]CCO>[Cl-].[NH4+]>[CH3:18][O:19][CH2:20][CH2:21][O:22][C:10]1[C:9]2[C:14](=[CH:15][CH:16]=[C:7]([CH:6]=[O:25])[CH:8]=2)[N:13]=[CH:12][CH:11]=1A mixture of butyl (4-chloro-quinolin-6-ylmethylene)-amine (preparation was described in example 27b) (250 mg, 1.01 mmol) and a solution of sodium (2-methoxy)-ethoxide in 2-methoxy-ethanol (2.5 mL, 10.0 mmol, 4.0M) were placed in a microwave tube and the mixture was heated to 120° C. for 30 min in a closed microwave. Then, the suspension was diluted with saturated ammonium chloride solution and the organic compound was extracted into ethyl acetate (3×50 mL). The combined extracts were washed with brine solution and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the solvent was removed under the vacuum and the brown residue was dissolved in THF (2 mL) and 1 mL of HCl solution (3.0N) was added. The resulting solution was stirred for 1 h at room temperature. Then, it was neutralized with potassium carbonate solution and extracted with ethyl acetate (2×50 mL). The combined extracts were washed with brine solution and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the solvent was removed under the vacuum and the brown residue was purified by using a Biotage silica gel column chromatography to obtain 160 mg (68.3% yield) of 4-(2-methoxy-ethoxy)-quinoline-6-carbaldehyde as a brown solid: EI-LRMS m/e calcd for C13H13NO3 (M+) 232.1, found 232.1.
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