反応 #160023

反応方程式

Benz[d]indeno[1,2-b]pyran-5,11-dione

1,6-diaminohexane

CHCl3

→

solid

収率 81.0%

6-(6-Aminohexyl)-5,6-dihydro-5,11-diketo-11H-indeno[1,2-c]isoquinoline Hydrochloride

収率 81.0%

反応条件

後処理

1. 1
   温度the reaction mixture was heated
2. 2
   温度at reflux for 16 h
3. 3
   洗浄washed with water (3×25 mL)
4. 4
   乾燥The solution was dried over sodium sulfate
5. 5
   ろ過filtered
6. 6
   workup.ADDITIONtreated with 2 M HCl in Et2O (5 mL)
7. 7
   ろ過the reaction mixture was filtered
8. 8
   洗浄the filter pad was washed with CHCl3 (50 mL) and hexanes (50 mL)

実験手順

Benz[d]indeno[1,2-b]pyran-5,11-dione (4d) (0.100 g, 0.403 mmol) was treated with 1,6-diaminohexane (0.234 g, 2.014 mmol) in CHCl3 (40 mL) and the reaction mixture was heated at reflux for 16 h. The reaction mixture was allowed to cool to room temperature and washed with water (3×25 mL). The solution was dried over sodium sulfate, filtered, and treated with 2 M HCl in Et2O (5 mL). After 30 min, the reaction mixture was filtered and the filter pad was washed with CHCl3 (50 mL) and hexanes (50 mL) to provide an orange solid (0.125 g, 81%): mp 195° C. (dec). IR (film) 3435, 1660, 1630, 1610, and 1504 cm−1; 1H NMR (CDCl3) δ 8.59 (d, J=7.8 Hz, 1H), 8.23 (d, J=8.1 Hz, 1H), 7.85-7.71 (m, 4H), 7.61-7.51 (m, 4H), 4.52 (t, J=7.3 Hz, 2H), 2.78 (m, 2H), 1.79 (m, 2H), 1.59-1.39 (m, 6H); ESIMS m/z (rel intensity) 347 (MH+, 100). Anal. (C22H23ClN2O2.0.5H2O) C, H, N.

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