3-(Trifluoromethyl)benzaldehyde → (2E)-3-(3-(trifluoromethyl)phenyl)prop-2-enal

3-Trifluoromethylbenzaldehyde (20.0 g, 0.115 mol) was taken up in 500 mL of CH3CN along with (triphenylphosphoranylidene)acetaldehyde (35 g, 0.115 mol). The reaction mixture was stirred at room temperature for 18 h. It was then concentrated under reduced pressure. The resulting residue was taken up in 800 mL of 1:1 pentane/EtOAc and filtered. The filtrate was concentrated under reduced pressure to afford crude (E)-3-(3-(trifluoromethyl)phenyl)acrylaldehyde as a dark red oil. This material was taken up in 30 mL of CH2Cl2. The resulting mixture was slowly added to a suspension of 2-nitroaniline (4 g, 0.029 mol) in concentrated HCl (50 mL) at 90° C. over a period of 30 min. The resulting reaction mixture was stirred at 90° C. for an additional 1 h. The reaction mixture was cooled to room temperature and washed with CH2Cl2 (2×100 mL). The aqueous layer was neutralized with 5% aqueous NaOH and extracted with CH2Cl2. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (pentane/EtOAc) to afford 800 mg of 8-nitro-2-(3-(trifluoromethyl)phenyl)quinoline. MS (ESI) calcd for C16H9F3N2O2 (m/z): 318.06. found: 319 [M+1].

1. concentrationIt was then concentrated under reduced pressure
2. filtrationfiltered
3. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-a819fac853d34d488821fc7c140aad22

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685970B2