Magnesium → HCID 69394141, compound

HRID 405896Notes

Reaction equation

HRID 405896 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

HCID 69394141HCID 69394141, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

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. 1 H), 7.25-7.30 (m, 1 H), 7.14 (d, J=7.6 Hz, 1 H), 6.93-7.01 (m, 3 H), 6.77-6.86 (m, 3 H), 4.36 (d, J=6.4 Hz, 1 H), 4.24 (d, J=6.4 Hz, 1 H), 4.18 (t J=5.5 Hz, 2 H), 3.78 (s, 3 H), 2.97 (t, J=5.6 Hz, 2 H), 2.19-2.24 (m, 2 H).

Workup

  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

Sources & evidence

ORD record
ord-85293a1757344b04876e56bec301d253
Source dataset
uspto-grants-2014_06
Patent number
US08754078B2

Reaction notes

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