Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
HRID 11061생성일: 2026년 10월 25일
p-Toluenesulfonic acid → 6-(2-Hydroxyethyl)-9-methoxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione
https://huagongshe.com/reaction/11061
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | p-Toluenesulfonic acid | HCID 6101 | — |
| 반응물 | Maleimide | HCID 10935 | — |
| 반응물 | 2-(2-Bromoethoxy)tetrahydro-2H-pyran | HCID 86621 | — |
| 반응물 | 2-[(e)-2-(2-Bromo-4-nitrophenyl)ethenyl]-5-methoxy-1h-indole | HCID 21980890 | — |
| 용매 | Methanol | HCID 887 | — |
| 용매 | Water | HCID 962 | — |
| 생성물 | 6-(2-Hydroxyethyl)-9-methoxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione | HCID 86760198 | — |
반응 단계
5-methoxy-2-[(E,Z)-2-phenylethenyl]-1H-indole (II; Ar=phenyl) (1.93 g, 7.74 mmol was reacted with 2-(2-bromoethoxy)tetrahydro-2H-pyran using the procedure described in example 38. This material was reacted directly with maleimide (0.79 g) using the procedure described in method 4. The product obtained was reacted using the procedure described in example 70 gave crude material that was then dissolved in methanol (100 mL) to which p-toluenesulfonic acid (30 mg) was added before the solution was warmed to 50° C. for 3h. The solution was then diluted with water and extracted with ethyl acetate. The organic phase was dried, the drying agent was removed and the solution was concentrated to dryness before being adsorbed onto silica and chromatographed eluting with ethyl acetate/hexane (1:2 to 1:1) to give 6-(2-Hydroxyethyl)-9-methoxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=phenyl, R10═(CH2)2OH) (201) in a yield of 0.51 g, 17% as a yellow powder; mp 262–264° C. 1H NMR δ [(CD3)2SO] 11.09 (br s, 1H), 8.56 (d, J=2.6 Hz, 1H), 7.83 (s, 1H), 7.66 (m, 3H), 7.47 (m, 3H), 7.28 (dd, J=9.0, 2.6 Hz, 1H), 4.86 (t, J=5.5 Hz, 1H), 4.55 (t, J=5.3 Hz, 2H), 3.90 (s, 3H), 3.78 (m, 2H). Found: C, 71.47; H. 4.77; N, 7.32. C23H18N2O4 requires: C, 71.49; H, 4.70; N, 7.25.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US07094798B1 |
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| 출처 데이터셋 | uspto-grants-2006_08 |
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| ORD ID | ord-3f6e1d2b349c474fa6a16a0f93f62613 |
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| 출처 메모 | uspto-grants-2006_08 |
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