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Magnesium → HCID 69394141, 화합물

HRID 388351
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HRID 388351 반응식
[C:1]1([C:13]2[C:14](=[O:27])[NH:15][C:16](=[O:26])[C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1.[Mg]>CO.C(OCC)(=O)C>[C:1]1([C@H:13]2[C@H:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=3)[C:16](=[O:26])[NH:15][C:14]2=[O:27])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1
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5

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HCID 5462224MagnesiumHCID 670170143-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(3-methoxyphenyl)-1H-pyrrole-2,5-dione

생성물 1

HCID 69394141HCID 69394141, 화합물

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(3-methoxyphenyl)-1H-pyrrole-2,5-dione (0.73 g, 2.04 mmol), magnesium (0.89 g, 36.7 mmol) in anhydrous methanol was heated to reflux for 1.5 h. After cooling to room temperature, the light yellow solution was diluted with ethyl acetate (200 mL), washed with 1.0 M hydrochloric acid (2×50 mL), water (100 mL), dried over sodium sulfate and concentrated to provide a light brown solid. The residue was purified by column chromatography on silica gel eluting with 40-50% ethyl acetate in hexane to yield (±)-trans-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(3-methoxyphenyl)pyrrolidine-2,5-dione as a light yellow solid. Mp 87-91° C.; 1H NMR (CDCl3) 400 MHz δ: 8.73 (s, 1H), 7.25-7.30 (m, 1H), 7.14 (d, J=7.6 Hz, 1H), 6.93-7.01 (m, 3H), 6.77-6.86 (m, 3H), 4.36 (d, J=6.4 Hz, 1H), 4.24 (d, J=6.4 Hz, 1H), 4.18 (t J=5.5 Hz, 2H), 3.78 (s, 3H), 2.97 (t, J=5.6 Hz, 2H), 2.19-2.24 (m, 2H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 h
  3. washwashed with 1.0 M hydrochloric acid (2×50 mL), water (100 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto provide a light brown solid
  7. customThe residue was purified by column chromatography on silica gel eluting with 40-50% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-c70c89e3a4a54fc29723f98e8cb4a6a7
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08377927B2

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