Hydrochloric Acid → HCID 10750851, compound

To a solution of 2-nitroacetamide ammonium salt (4 g, 33 mmol) in water (165 mL) was added piperidinium acetate (33 mmol) in water followed by slow addition of 4-ethoxy-1,1,1-trifluoro-3-buten-2-one (6.1 mL, 43 mmol) in MeOH (11 mL). The reaction was stirred for 2 h at room temperature and at reflux for 3 h. The reaction mixture was allowed to cool to 45° C. and aqueous HCl (1N) was added until the pH was acidic. After 1 h at room temperature, the reaction mixture was extracted with CH2Cl2 (3×). The combined organic layer was successively washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (EtOAc, then EtOAC:MeOH, 9:1) to give 3-nitro-6-(trifluoromethyl)-2(1H)-pyridinone (2.7 g, 40% yield) as a yellow solid.

1. temperatureat reflux for 3 h
2. temperatureto cool to 45° C.
3. waitAfter 1 h at room temperature
4. extractionthe reaction mixture was extracted with CH2Cl2 (3×)
5. washThe combined organic layer was successively washed with water and brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by flash chromatography (EtOAc

ORD record

ord-b8f1b9a8a1e64190866e938fe34f56fa

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06420359B1