Ethyl Acetate → HCID 58009999、化合物

6-Chloro-4-(trifluoromethyl)nicotinic acid (1.0 g, 4.4 mmol, Oakwood) was dissolved in DCM (44 mL) to give a clear solution. SOCl2 (3.2 mL, 44 mmol) was added drop-wise and the reaction mixture was stirred at room temperature overnight and then at reflux for about 16 h. The mixture was concentrated under reduced pressure to give a yellow oil that was dissolved into EtOAc (10 mL). The solution was added drop-wise to a rapidly stirred mixture of EtOAc (20 mL) and concentrated aqueous NH4OH (22 mL, 580 mmol). The resulting cloudy mixture was stirred for about 2 h and separated. The aqueous layer was further extracted with EtOAc (30 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give 6-chloro-4-(trifluoromethyl)nicotinamide (0.85 g, 85%) as off-white solid: LC/MS (Table 2, Method a) Rt=1.62 min; MS m/z: 223 (M+H)+.

1. customto give a clear solution
2. temperatureat reflux for about 16 h
3. concentrationThe mixture was concentrated under reduced pressure
4. customto give a yellow oil that
5. additionThe solution was added drop-wise
6. stirringThe resulting cloudy mixture was stirred for about 2 h
7. customseparated
8. extractionThe aqueous layer was further extracted with EtOAc (30 mL)
9. washThe combined organic extracts were washed with brine
10. dry with materialdried over anhydrous Na2SO4
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure

ORDレコード

ord-a54309c8f5ff4ac0b10a249304c82047

出典データセット

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09365579B2