反応 #11224

反応方程式

anhydride

4-(2-Chlorophenyl)-9-methoxy-4,5,6,10c-tetrahydro-1H-furo[3,4-c]carbazole-1,3(3aH)-dione

2,4-dimethoxybenzylamine

→

4-(2-Chlorophenyl)-2-(2,4-dimethoxybenzyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

溶媒

acetic acid

反応条件

後処理

1. 1
   温度The resulting solution was heated
2. 2
   温度at reflux for 6 hours
3. 3
   濃縮before being partially concentrated under reduced pressure
4. 4
   workup.ADDITIONdiluted with water
5. 5
   その他to precipitate an orange solid, which
6. 6
   ろ過was collected by filtration
7. 7
   洗浄washed with water
8. 8
   その他dried in vacuo
9. 9
   workup.DISSOLUTIONThis crude material was then dissolved in p-dioxane
10. 10
    その他before being chromatographed on silica eluting with ethyl acetate/hexane (1:1)
11. 11
    その他Crystallisation from methanol

実験手順

To a solution of anhydride (286) (2.80 g, 7.42 mmol) prepared as described in example 296 in glacial acetic acid (70 mL) was added 2,4-dimethoxybenzylamine (1.67 mL, 11.1 mmol). The resulting solution was heated at reflux for 6 hours before being partially concentrated under reduced pressure and diluted with water to precipitate an orange solid, which was collected by filtration, washed with water and dried in vacuo. This crude material was then dissolved in p-dioxane and aromatized according to the procedure for example 79, before being chromatographed on silica eluting with ethyl acetate/hexane (1:1). Crystallisation from methanol then gave carbazole (287) (1.46 g, 37%) as a yellow powder, mp 224–226° C. 1H NMR δ [(CD3)2SO] 12.02 (br s, 1H), 8.45 (d, J=2.6 Hz, 1H), 7.62 (s, 1H), 7.58 (m, 2H), 7.53–7.42 (m, 3H), 7.25 (dd, J=8.8, 2.6 Hz, 1H), 6.95 (d, J=8.4 Hz, 1H), 6.57 (d, J=2.3 Hz, 1H), 6.45 (dd, J=8.4, 2.3 Hz, 1H), 4.68 (s, 2H), 3.88 (s, 3H), 3.80 (s, 3H), 3.72 (s, 3H). Found: C, 68.22; H, 4.37; N, 5.29. C30H23ClN2O5 requires: C, 68.38; H, 4.40; N, 5.32.

出典