反応 #82711

反応方程式

2-(3-nitrophenylmethylene)cyclohexanone

1,3-cyclohexanedione

ammonium acetate

→

title compound

収率 7.6%

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

収率 7.6%

溶媒

ethanol

反応条件

後処理

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

実験手順

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.

出典