反应详情

温度

100 °C

A mixture of 1.0 g (5.0 mmol) 1-(2-amino-4-(trifluoromethyl)phenyl)ethanone, 3.4 ml (25.0 mmol) ethyl 3-chloro-3-oxopropanoate and 435 μl (5.0 mmol) conc. hydrochloric acid was heated in a sealed vessel in the MW to 100° C. for 30 min. The mixture was subsequently diluted with EtOAc and water. The organic phase was separated, washed with a 1M aq. NaHCO3 sol., dried over MgSO4 and concentrated in a vacuum. The raw product (1.14 g) obtained after CC (EtOAc/hexane 3:17) of the residue was dissolved in MeCN (6 ml) and 2.7 ml (15.5 mmol) DIPEA and 838 mg (10.3 mmol) dimethylammoniumchlorid were added. The mixture was subsequently stirred at RT for 16 h. After cooling to RT, the mixture was diluted with water and extracted with EtOAc. The organic layer was extracted twice a 2N aq. HCl and water. The combined aqueous layers were basified with Na2CO3 and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuum. As residue 776 mg (2.3 mmol, 46%) 2-((dimethylamino)methyl)-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester was obtained.

1. customThe organic phase was separated
2. washwashed with a 1M aq. NaHCO3 sol.
3. dry with materialdried over MgSO4
4. concentrationconcentrated in a vacuum
5. customThe raw product (1.14 g) obtained after CC (EtOAc/hexane 3:17) of the residue
6. temperatureAfter cooling to RT
7. extractionextracted with EtOAc
8. extractionThe organic layer was extracted twice a 2N aq. HCl and water
9. extractionextracted with EtOAc
10. washThe organic layer was washed with brine
11. dry with materialdried over MgSO4
12. concentrationconcentrated in vacuum