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

HRID 72841

반응식

HRID 72841 반응식
[CH:1]1[C:6]2[C:7]3[C:18](=O)[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:8]=3[O:9][C:10](=[O:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[NH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][NH2:27].C(Cl)(Cl)[Cl:29]>>[ClH:29].[NH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[C:7]2[C:6]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:10](=[O:11])[C:18]=2[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:8]1=[O:9]

참가 물질

4

반응물 3

HCID 6212ChloroformHCID 16402HexamethylenediamineHCID 265728Indeno(1,2-c)isochromene-5,11-dione

생성물 1

HCID 162213206-(6-Aminohexyl)-5,6-dihydro-5,11-diketo-11H-indeno[1,2-c]isoquinoline Hydrochloride수율 81%

실험 절차

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.

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. washwashed with water (3×25 mL)
  4. dry with materialThe solution was dried over sodium sulfate
  5. filtrationfiltered
  6. additiontreated with 2 M HCl in Et2O (5 mL)
  7. filtrationthe reaction mixture was filtered
  8. washthe filter pad was washed with CHCl3 (50 mL) and hexanes (50 mL)

출처 및 근거

ORD 기록
ord-c1299629dfc742f6b7c91ed7223cee6d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829022B2

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