تفاعل #160023

معادلة التفاعل

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

1,6-diaminohexane

CHCl3

→

solid

المردود 81.0%

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

المردود 81.0%

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture was heated
2. 2
   درجة الحرارةat reflux for 16 h
3. 3
   غسيلwashed with water (3×25 mL)
4. 4
   تجفيفThe solution was dried over sodium sulfate
5. 5
   ترشيحfiltered
6. 6
   workup.ADDITIONtreated with 2 M HCl in Et2O (5 mL)
7. 7
   ترشيحthe reaction mixture was filtered
8. 8
   غسيلthe filter pad was washed with CHCl3 (50 mL) and hexanes (50 mL)

الإجراء التجريبي

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.

المصدر