Triethylamine → 7H-1,3-Benzodioxolo[4,5-f]isoindole-7,9(8H)-dione, 10-(1,3-benzodioxol-5-yl)-8-hydroxy-

HRID 2354598Notes

Reaction equation

HRID 2354598 reaction equation
Cl.[OH:2][NH2:3].C(N(CC)CC)C.[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]3[C:21]4[C:35](=[O:36])[O:34][C:33](=O)[C:22]=4[CH:23]=[C:24]4[C:32]=3[C:28]3[O:29][CH2:30][O:31][C:27]=3[CH:26]=[CH:25]4)=[CH:19][C:14]=2[O:13][CH2:12]1>CCO>[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([C:20]3[C:32]4[C:24](=[CH:25][CH:26]=[C:27]5[O:31][CH2:30][O:29][C:28]5=4)[CH:23]=[C:22]4[C:33](=[O:34])[N:3]([OH:2])[C:35](=[O:36])[C:21]=34)=[CH:19][C:14]=2[O:13][CH2:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 527377710-Benzo[1,3]dioxol-5-yl-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxole-7,9-dione

Product 1

HCID 52737977H-1,3-Benzodioxolo[4,5-f]isoindole-7,9(8H)-dione, 10-(1,3-benzodioxol-5-yl)-8-hydroxy-Yield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxyamine hydrochloride (20.9 mg, 0.3 mmol) and triethylamine (0.04 mL, 0.3 mmol) were dissolved in EtOH (30 mL). After stirring for 10 min, anhydride 1 (109 mg, 0.3 mmol) was added. The mixture was refluxed overnight and then concentrated in vacuo. The resulting product was purified by silica gel column chromatography using CH2Cl2/acetone (2:1, v/v) to afford 24 (16 mg, 15%) as a yellow powder. mp 255° C. (decomp.); 1H NMR (DMSO-d6) δ 10.78 (s, 1H, OH), 8.40 (s, 1H, H4), 7.89 (d, 1H, H5, J=8.7 Hz), 7.54 (d, 1H, H6, J=8.7 Hz), 6.94 (s, 1H, H2′), 6.90 (d, 1H, H5′, J=7.8 Hz), 6.79 (d, 1H, H6′, J=7.8 Hz), 6.08 (s, 2H, 3′,4′-OCH2O—), 5.96 (AB, 2H, 7,8-OCH2O—, Δδ=5.7 Hz); MS (FAB, positive) m/z 378 [M+H]+.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. concentrationconcentrated in vacuo
  3. customThe resulting product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-59a414257744457e80eca91ec6469690
Source dataset
uspto-grants-2010_07
Patent number
US07754718B2

Reaction notes

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