Dimethylformamide → 4-(2-Dimethylamino-ethoxy)-quinoline-6-carbaldehyde

To a solution of 2-dimethyamino-ethanol (500 mg, 5.61 mmol) in DMF (N,N-dimethylformamide) (30 mL) was added sodium hydride (161.5 mg, 6.73 mmol, 1.2 equiv.) at 0° C. and stirred for 15 min at this temperature. Then, a solution of butyl (4-chloroquinolin-6-ylmethylene)-amine (preparation was described in example 27b) (553.6 mg, 2.24 mmol) in DMF (5 mL) was added at 0° C. After addition, the reaction mixture was allowed to warm to room temperature and stirred for 15 h. Then, the mixture 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 (4 mL) and 6 mL of HCl solution (3.0N) was added. The resulting solution was stirred for 3 h at room temperature. Then, it was neutralized with sodium bicarbonate 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 155 mg (11.3% yield) of 4-(2-dimethylamino-ethoxy)-quinoline-6-carbaldehyde as a brown solid: EI-HRMS m/e calcd for C14H16N2O2 (M+) 244.1212, found 244.1213.

1. additionAfter addition
2. stirringstirred for 15 h
3. extractionthe organic compound was extracted into ethyl acetate (3×50 mL)
4. washThe combined extracts were washed with brine solution
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationAfter filtration of the drying agent
7. customthe solvent was removed under the vacuum
8. dissolutionthe brown residue was dissolved in THF (4 mL)
9. addition6 mL of HCl solution (3.0N) was added
10. stirringThe resulting solution was stirred for 3 h at room temperature
11. extractionextracted with ethyl acetate (2×50 mL)
12. washThe combined extracts were washed with brine solution
13. dry with materialdried over anhydrous magnesium sulfate
14. filtrationAfter filtration of the drying agent
15. customthe solvent was removed under the vacuum
16. customthe brown residue was purified

ORD record

ord-6afd06b019954571ad73ceaa77efd9a0

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07253285B2