ETHYL 4-HYDROXY-7-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLATE synthesis
- Product Name:ETHYL 4-HYDROXY-7-(TRIFLUOROMETHYL)QUINOLINE-3-CARBOXYLATE
- CAS Number:391-02-6
- Molecular formula:C13H10F3NO3
- Molecular Weight:285.22
Yield:391-02-6 93%
Reaction Conditions:
at 125; for 1 h;
Steps:
1 Ethyl 4-hydroxy-7-(trifluoromethyl)quinoline-3-carboxylate [MM-I-04].
3-(Trifluoromethyl)aniline (10 g, 62.1 mmol) was heated with diethyl ethoxymethylene malonate (12.6 mL, 62 mmol) at 125 °C for 1 h. Then, downtherm A (50 mL) was added and the mixture was heated up to 255 °C for 2.5 h. After heating, the reaction was brought to room temperature and diluted with hexane (50 mL). The mixture was stirred for 5 min. The precipitated was filtered and washed with hexane to provide the product as a white colored solid MM-I-04 (16.51 g, 93%): mp 340- 341 °C; 1H NMR (300 MHz, DMSO) δ 12.51 (s, 1H; H-11), 8.70 (s, 1H; H-8), 8.35 (d, J = 8.3 Hz, 1H; H-6), 8.00 (s, 1H; H-3), 7.72 (d, J = 8.1 Hz, 1H; H-1), 4.24 (q, J = 14.3, 7.1 Hz, 2H; H-20), 1.29 (t, J = 7.0 Hz, 3H; H-19); HRMS m/z calculated for C13H10NO3F3286.0686 found 286.0691.
References:
WO2016/196961,2016,A1 Location in patent:Paragraph 00147
![diethyl [(alpha,alpha,alpha-trifluoro-m-toluidino)methylene]malonate](/CAS/GIF/370-35-4.gif)
370-35-4
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