Reacción #82711

Ecuación de reacción

2-(3-nitrophenylmethylene)cyclohexanone

1,3-cyclohexanedione

ammonium acetate

→

title compound

Rendimiento 7.6%

9-(3-Nitrophenyl)-3,4,5,6,7,8,9,10-octahydro-1(2H)-acridinone

Rendimiento 7.6%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux under nitrogen for 48 hours
2. 2
   TemperaturaThe mixture was cooled in an ice bath
3. 3
   Filtraciónorange crystals were collected by filtration
4. 4
   OtroThe material was chromatographed with dichloromethane, ethyl ether:dichloromethane (2:98) and ethyl ether:dichloromethane (10:90) as the elutents
5. 5
   OtroThe solvent was evaporated
6. 6
   Otrothe residue recrystallized from toluene/hexane

Procedimiento

A mixture of 2-(3-nitrophenylmethylene)cyclohexanone (4.69 g), 1,3-cyclohexanedione (2.28 g), ammonium acetate (2.35 g) and 90 mL of ethanol was stirred at reflux under nitrogen for 48 hours. The mixture was cooled in an ice bath and orange crystals were collected by filtration. The material was chromatographed with dichloromethane, ethyl ether:dichloromethane (2:98) and ethyl ether:dichloromethane (10:90) as the elutents. The solvent was evaporated and the residue recrystallized from toluene/hexane to yield the title compound as yellow crystals (0.50 g); mp 218°-221° C.; NMR (CDCl3): 1.57-1.59 (m,4, CH2) 1.74-1.80 (m,2, CH2) 1.88-2.01 (m,2, CH2) 2.14 (broad s,2, CH2) 2.28-2.36 (m,2, CH2) 2.42-2.46 (m,2, CH2) 4.50 (s,1, CH) 5.40 (s,1, NH) 7.38 (t,1, J=7.8, Ar) 7.71 (d,1, J=7.6, Ar) 7.98 (q,1, J=7.3, 1.4, Ar) 8.09 (d,1, J=1.9, Ar); MS (CI, CH4): m/z=325(M+1). Analysis for C19H20N2O3.0.6 H20:Calculated: C, 68.08; H, 6.37; N, 8.36; Found: C, 68.27; H, 6.28; N, 8.01.

Fuente