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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

반응식

참여 물질

역할이름HCID투입량
반응물p-Toluenesulfonic acidHCID 6101—
반응물MaleimideHCID 10935—
반응물2-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 86621—
반응물2-[(e)-2-(2-Bromo-4-nitrophenyl)ethenyl]-5-methoxy-1h-indoleHCID 21980890—
용매MethanolHCID 887—
용매WaterHCID 962—
생성물6-(2-Hydroxyethyl)-9-methoxy-4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneHCID 86760198—

반응 조건

온도50 °C

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

DOI10.6084/m9.figshare.5104873.v1
특허 번호US07094798B1
출처 데이터셋uspto-grants-2006_08
ORD IDord-3f6e1d2b349c474fa6a16a0f93f62613
출처 메모uspto-grants-2006_08