3-Nitro-6-(trifluoroMethyl)pyridin-2(1H)-one synthesis
- Product Name:3-Nitro-6-(trifluoroMethyl)pyridin-2(1H)-one
- CAS Number:117519-07-0
- Molecular formula:C6H3F3N2O3
- Molecular Weight:208.09
14011-21-3
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117519-07-0
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Yield:117519-07-0 5.5 g
Reaction Conditions:
with sodium ethanolate in ethanol at 90; for 2 h;
Steps:
45.B B)
3-nitro-6-(trifluoromethyl)pyridin-2-ol
B)
3-nitro-6-(trifluoromethyl)pyridin-2-ol
To a solution of 2-nitroacetamide (16.9 g) and (3E)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one (30.0 g) in ethanol (700 mL) was slowly added sodium ethoxide (22.1 g) at room temperature.
The reaction mixture was stirred at 90°C for 2 hr, the pH of the mixture was adjusted to 2 with 1 M hydrochloric acid, and the mixture was stirred at room temperature for additional 30 min.
To the reaction mixture was added water, and the mixture was extracted with ethyl acetate.
The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (5.5 g).
1H NMR (400 MHz, CDCl3) δ 7.46 (1H, d, J = 8.0 Hz), 8.69 (1H, d, J = 8.0 Hz), 11.02 (1H, brs).
References:
Takeda Pharmaceutical Company Limited;MIKAMI, Satoshi;NAKAMURA, Shinji;ASHIZAWA, Tomoko;SASAKI, Shigekazu;TANIGUCHI, Takahiko;NOMURA, Izumi;KAWASAKI, Masanori EP2848618, 2015, A1 Location in patent:Paragraph 0651
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117519-07-0
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$54.00/100mg