Acetic Acid → Acetamide, N-[10-(1,3-benzodioxol-5-yl)-7,9-dihydro-7,9-dioxo-8H-1,3-benzodioxolo[4,5-f]isoindol-8-yl]-

HRID 2354599Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11]4[C:25](=[O:26])[O:24][C:23](=O)[C:12]=4[CH:13]=[C:14]4[C:22]=3[C:18]3[O:19][CH2:20][O:21][C:17]=3[CH:16]=[CH:15]4)=[CH:9][C:4]=2[O:3][CH2:2]1.O.[NH2:29][NH2:30].[C:31]([OH:34])(=O)[CH3:32]>>[O:21]1[C:17]2[CH:16]=[CH:15][C:14]([C:13]3[C:9]4[C:8](=[CH:7][CH:6]=[C:5]5[O:1][CH2:2][O:3][C:4]5=4)[CH:10]=[C:11]4[C:25](=[O:26])[N:29]([NH:30][C:31](=[O:34])[CH3:32])[C:23](=[O:24])[C:12]=34)=[CH:22][C:18]=2[O:19][CH2:20]1

Participants

Reactant 3

HCID 176Acetic Acid

HCID 24654Hydrazine hydrate (1:1)

HCID 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 5273798Acetamide, N-[10-(1,3-benzodioxol-5-yl)-7,9-dihydro-7,9-dioxo-8H-1,3-benzodioxolo[4,5-f]isoindol-8-yl]-Yield 86%

Procedure

A solution of anhydride 1 (145 mg, 0.4 mmol) in glacial acetic acid (10 mL) was refluxed with hydrazine hydrate (0.023 mL, 0.48 mmol) for 24 h under nitrogen and then poured, after cooling, into ice water. The resulting precipitate was filtered and dried under reduced pressure. The residue was purified by column chromatography on silica gel using CH2Cl2/MeOH (30:1 to 20:1, v/v) to give 25 (143 mg, 86%) as a yellow solid. mp 281-283° C.; 1H NMR (CDCl3) δ 8.34 (s, 1H, H4), 7.69 (d, 1H, H5, J=8.7 Hz), 7.46 (s, 1H, NHAc), 7.38 (d, 1H, H6, J=8.7 Hz), 6.84-6.87 (m, 3H, H2′+H5′+H6′), 6.06 (AB, 2H, 3′,4′-OCH2O—, Δδ=16.5 Hz, J=1.5 Hz), 5.98 (AB, 2H, 7,8-OCH2O—, Δδ=5.4 Hz, J=1.2 Hz), 2.17 (s, 3H, NHCOCH3); MS (EI) m/z 418 [M]+.

Workup

additionpoured
filtrationThe resulting precipitate was filtered
customdried under reduced pressure
customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-9982b5b4fa1d45f6b2d0c2467f1f04fb
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754718B2

Reaction notes

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