Reacción #82739

Ecuación de reacción

methylene chloride ether

ethyl ether hexane

water

(-)-4-(3-cyanophenyl)-2-trifluoromethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid

→

title compound

Rendimiento 99.0%

(-)-4-(3-Cyanophenyl)-2-trifluoromethyl-4,6,7,8-tetrahydro-5 (1H)-quinolone

Rendimiento 99.0%

Disolventes

N-methylpyrrolidin-2-one

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe cooled reaction mixture
2. 2
   Extracciónextracted twice with ethyl ether
3. 3
   LavadoThe combined ether extracts were washed twice with water
4. 4
   Secadodried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Otrothe solvent removed
7. 7
   Otroto yield an off-white solid

Procedimiento

A stirred solution of (-)-4-(3-cyanophenyl)-2-trifluoromethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylic acid (3.93 g, 10.85 mmol) in N-methylpyrrolidin-2-one (24 mL) was placed in a preheated oil bath at 210° C. for 20 minutes. The cooled reaction mixture was then poured into water (200 mL) and extracted twice with ethyl ether. The combined ether extracts were washed twice with water, dried (MgSO4), filtered and the solvent removed to yield an off-white solid. Chromatography (eluent: methylene chloride/ether 9:1) and trituration with ethyl ether/hexane provided the title compound (3.42 g, 79%) as a white solid mp 187°-189° C. NMR: 1.88-1.91 (m,2H, CH2), 2.21-2.25 (m,2H, CH2), 2.53-2.64 (m,2H, CH2), 4.68(d,1H, J=5.3 Hz, CH), 5.61 (d,1H, J=5.3 Hz, CH), 7.50-7.54 (m,2H, Ar), 7.61-7.66 (m,2H, Ar), 9.42 (s,1H, NH); MS: m/z=319(M+1); [α]D23 =-606.8° (c=0.665 methanol). Analysis for C17H13F3N2O: Calculated: C, 64.14; H, 4.12; N, 8.80; Found: C, 64.07; H, 4.24; N, 8.78.

Fuente