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

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Hydroxyamine hydrochloride	HCID 443297	—
Reactant	10-Benzo[1,3]dioxol-5-yl-furo[3',4':6,7]naphtho[1,2-d][1,3]dioxole-7,9-dione	HCID 5273777	—
Solvent	Ethanol	HCID 702	—
Product	7H-1,3-Benzodioxolo[4,5-f]isoindole-7,9(8H)-dione, 10-(1,3-benzodioxol-5-yl)-8-hydroxy-	HCID 5273797	15%

Reaction Steps

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]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07754718B2
Source dataset	uspto-grants-2010_07
ORD ID	ord-59a414257744457e80eca91ec6469690
Source note	uspto-grants-2010_07